The future of internships, apprenticeships and learning on the job with Matt Wilkerson of Paragon One

The future of internships, apprenticeships and learning on the job with Matt Wilkerson of Paragon One

Join Maren for today’s conversation with Matt Wilkerson, CEO of Paragon One. We’ll chat about education in a post-COVID-19 world, how higher education can reinvent itself and what recent grads can do to improve their chances in today’s job market.

You can find Matt online @mwilker on Twitter, on LinkedIn, and at

Photo of Matt Wilkerson
Matt Wilkerson

The CEO of Paragon One, which is a remote career coaching platform that recreates the internship experience by pairing top executives with students in higher education to help them find internships and jobs.

Maren Kate 0:00

So today's guest is Matt Wilkerson. He's currently co founder and CEO of Paragon one and previously co founded the e commerce platform. Aha life calm. Mike. Matt is also an angel investor in companies such as classpass, Bevy and mogul and got his start in banking and VC. Matt, welcome to the show. And apologies. I'm like choking on something right now.

Matt Wilkerson 0:24

No worries. Well, welcome and welcome. Thank you for welcoming.

Maren Kate 0:30

Absolutely. So just in 60 seconds or less. Obviously, you founded companies before and you know, been on the finance side of things. What made you you and your co founder come up with the idea for Paragon one? And when did you guys start?

Matt Wilkerson 0:49

Yeah, well, my co founder and I, we've known each other since college. We were studying engineering at MIT. But my first job out of college worked in banking at Morgan Stanley was an analyst Got tendinitis in my hands from typing so much day and night. I didn't know how I could be valuable as an analyst who can't type. So I decided to sit behind the interns, and teach them and coach them and mentor them on how to do their jobs better. So by the end of that summer, they were so good at what they did, that they all got offers to come back into that group full time. And that was rare. So I kind of hung on to that idea later and said, Well, if you could harness the resources of companies to actually train students and educate them on real skills, that's how education should be.

Maren Kate 1:39

Yeah, absolutely. So that dives right in. First of all, like I've always loved working with interns, and I've done that before years ago. So from a company standpoint, especially in our current economy right now, how when you're pitching what you guys do to a founder or a CEO Like how do you explain the benefits that that tapping into this massive pool of talent?

Matt Wilkerson 2:07

What gives to people?

Yeah, well, so basically, I guess kind of I'll, I'll connect the dots here when we took this idea in many layers. Many years later, we launched Paragon one, originally as a on demand career coaching platform to help students get internships and jobs. And along the way, we, we said, well, its students, we're trying to help them get placed into some of these companies when they finished our program. And it was a lot of work. It's, you know, some students had good resumes, others didn't. Some students, maybe had better connections. And so there's a lot of things at play helping a student land an internship or job. And we asked the question, What if you could just recreate the internship experience for them Between a company and students. And that's what led to what we're doing now. So we pivoted last year, and we're providing what we call remote, call them remote externships. They're like internships, they're just shorter, more flexible, and have a structured training. But what we do is we go to companies, and what we're helping to educate them on is you can have interns and a more efficient way or you can have students working with you in a more efficient way. Because most companies they think that this is it is to be honest, in a lot of ways. It's such a huge lift takes so much effort and resource for them to recruit, train and manage students most don't do it, or they only take a few students. So that creates what we call this inventory constraint issue. So it's still early we're educating a lot of companies and finding the companies that want to take that leap and try this out.

Maren Kate 3:55

Why a why work with interns versus Hiring traditional staff or plug into like groups of freelancers?

Matt Wilkerson 4:06

Great question. The first thing I would say is, first of all, if you're if you're small or sorry, small to medium enterprise, up to a large enterprise, you probably have a real recruiting need. And you have a funnel that, at least for some of that funnel, you're going to want Junior talent. And so having a really engaged group of students that you can pull on is important. And if it's what's even better is if those students have been essentially getting assessed. Right. If you have a bunch of students, you've been assessing them, it's lower risk for you to know who to hire. And, and the other pitch I give the companies is that, you know, it, it is, this is what you should be doing for society, right? You should be giving young people a chance to learn, they learn about your brand, it spreads. So there's a lot reasons that I think companies are waking up to.

Maren Kate 5:03

What? What do you see is the difference between internships or what you're calling externships and apprenticeships? The like the apprenticeship model that, you know, we've had for 1000 years? Is it just a evolution of it? Or are those two separate types of models?

Matt Wilkerson 5:20

Yeah, well, we thought a lot about this as well, like what do we call what we do? And we we briefly thought about apprenticeships, apprenticeships, I think people considered like you said the old like, I'm learning a very practical skill, very hands on maybe I'm happy with this dedicated mentor, model shadowing them and doing their work with them. Internships have a pretty we've learned have a pretty well understood construct. You're going to go somewhere usually for a summer, you're going to usually sit in the office, you're going to get a lot of time with the company and hand holding and mentorship but It might be you might be one of many students doing it. externships actually has a definition. It's usually when a school partners with a company and students are doing a work like program for credit, usually. And we've sort of taken that term and we've kind of adapted it a bit what we call externship. Now in the remote world, remote externships is something where a school usually might be involved doesn't have to be, but some there is some kind of structure around it. They're more flexible than an internship, you can do them from anywhere. There's that that's the need. Now you've got to be able to fit into student's schedule, not just summer, something they can do year round. So usually ours are like 10 hours a week. They're also more accessible. They're meant to be more widely accessible from students that maybe don't go to an Ivy League school or don't have a fancy resume. So we're working with a lot of programs that work with underserved student communities. There. And then finally, they have structured training. We think that's very important students need to have some level of training. The real world itself is training but something that most companies can't usually offer is that level of training.

Maren Kate 7:17

So with like, I was looking at the site and some of the things you offered literally thinking about one of my companies how we need it is around social media and and SEO. So if you know, we plug it First of all, is there like a minimum commitment? What does that look like for a company like mine? And then I'd love to understand a little bit more about just the structure for for the interns and how they're learning.

Matt Wilkerson 7:45

Sure. So for companies, we've been experimenting with a few different models, but one most recently we've been doing as well, we might have kind of a monthly engagement. And in that case, we will have certain predefined templates, what we call project templates, because we don't do everything right. We don't we don't do for instance highly technical work. We don't do coding. That takes a lot of bandwidth of someone's time. But But yes, things like social media content SEO content, or data analysis work or research for business development, there's, there's certain projects that we we have templates for, that we can get up and going quickly, we can create training, and we can manage the workflow for you. So what works well with us are these sorts of content data research type projects that are evergreen. And it just sort of depends on you know, the, the model that we work with kind of just depends on how much work they need, how many students they want. The other model that we have is where we actually go to education institutions. So that might be for instance, we work with Swarthmore or Case Western or we work with some high schools. We also work with nonprofits like the Opportunity Network, which works with underserved communities. We'll go to them and we'll say, look, if you can sponsor some of your students, then we'll go back to our companies on our platform, who may only you know, have been able to pay for five students or 10 students, but we'll be able to go to our education partners and say, Look, if you can sponsor 50 to 100 students will actually let them will actually give them the training and the mentorship to work on these projects. And we do that a lot with with our bigger company partners like Facebook, Zillow, and others where they have teams within there are multiple teams sometimes that want to work on these projects. And we can have larger groups of students do that work who wouldn't normally get a chance because of so many other you know, things that are in their way.

Maren Kate 9:50

Okay, so for for students, um, or honestly for anyone that is like you think of internships or apprenticeships and anyone that's coming into the workforce that either doesn't have a lot of experience period, or doesn't have a lot of recent experience. So maybe you've stayed home and raised your kid for 14 years, or maybe you are, you know, a senior in college or maybe you just graduated high school, um, how, you know, if you were talking to a friend or a friend's kid, and you were a guy and they will fall that fell into either of those buckets. How would you advise them like, how do they go about that, especially in today's economy where, you know, there's a ton of unemployment and the markets pretty competitive now from tap for talent?

Matt Wilkerson 10:47

Yep. Great question. And we've seen even in some of our cases, people that had yet graduated been out of college a few years wanting to pivot wanting to try something new out the best way. First of all, just understand that these terms that we throw around in turn x turn, apprentice mean, these are just terms, right? You can call it whatever you want. But the advice I would give is, don't be afraid to think of just how you can provide value. And you don't mean it's kind of bring yourself out of the construct of, oh, I've got to go to a job board. I've got to apply to this listing. And if there's no listings, I can't apply. And if I'm applying for this full time, job opportunity, I mean, you've got to you got to wedge yourself in. And when I thought about the best people that I've ever hired, almost so many of them started off by cold emailing me. And, and sometimes we didn't even have a job posting, but they cold emailed me and they had, you know, wasn't a super long email wasn't an essay, but it was something that they had studied about what we're doing And a place they thought they could help. And saying look, can I do XYZ or maybe they went ahead and did something and they decided to share it with me. Right? And look, maybe you do this a few times and you don't hear back but I can tell you that if you rank the ways to get in touch with someone like sending your resume through a job board is like one of the like on the bar yep 100% look I mean I've got we've got Angeles postings up I don't check those hardly ever. But when someone in fact this is and I say this like my implicit screening is to put a job posting up and the people that actually email me or even just try to LinkedIn me and and that and then send me the resume and tell me about why they're passionate. Those are the people I interview first and they tend to be the best people to hire.

Maren Kate 12:52

Absolutely. I mean, in the the books that I'm writing right now going remote, one of the things that where I'm talking About is exactly that is like, Listen, don't just spray and pray don't apply to a bunch of positions and then expect the you know, people to get back to you. That's a that's very few people are run like a really tight hiring and recruiting process because everyone's doing a bunch of different things at the same time. And even when they do, especially now, especially for remote roles, you know, a good job will get 500 to 1000 applicants. So it's like, how do you stand out? And it's kind of amazing that it still boggles my mind that in education, our education system, whether it's, you know, whatever kid education is, clearly it'll have kids. So my kid education and college, we don't teach young people how to we don't teach young people how to get jobs or how to think through their career. We're like, we spent all this time teaching you know, you learn economics, you go to school for engineering or Me English Lit and then you drop out and do something completely different. But we don't teach like, Okay, this is how you get a job. This is how you position yourself like a lot of what we're writing in this book is thinking around like, how can you reframe the professional as a product and apply product positioning product marketing to yourself. And that's the simple the simple thing that most of I think less than 5% of applicants will use something like signal higher or anything to find your email and email you directly and say, Hey, I saw this post, or Hey Marin, I love what you're doing. And I, I'm a copywriter, and I'd love to do XYZ or here's an example of how I reword some of your copy. I've had people do that. I'm like, great, like, cool. I'll give you a shot like, go do X, Y. It's like, at the end of the day, I feel like especially when people are early in their career, maybe jumping back into To the job market, but no matter what you have to make it easy for other people to say yes, we almost have this, we have this misguided idea that like the hiring manager, or the person on the other side of the table will see like how we're the special little unicorn versus making it very clear and being like, this is what I can do for you.

Matt Wilkerson 15:22

Yeah. Now, this Yuria you're speaking, you're speaking my language because it you school universities and schools, they don't teach any of this stuff. There was like three three things people care most about, most generally speaking, and like the humanistic world, it's like, you know, money, getting getting a job managing your money and relationships and the schools don't teach you anything about this. So you and this is what we were trying to do before we pivoted as we were doing what we called on demand career coaching or career center as a service and a lot of schools. You know, they've Look, we've got a career center, we do this stuff, but there wasn't kind of like this extra layer. And that's just because higher education isn't set up that way, right? It's not set up. Originally, if you go back to what were higher education was set up, it was set up to produce research right? At the end. So PhD students produce research and you got to go at the goal, you got to you got to, it's like, well, if you don't make it to PhD, well, we'll give you this Master's. And if you don't make it there, we'll give you this thing called a bachelor's degree. And maybe that'll be worth something real world like, bye, bye. And that's that's how higher education was set up originally. And it never it. What you were taught to get the bachelors was just supposed to be a assessing greeting, yes, a stepping stone and a screening tool to see who could make it to PhD. And then they just left it that way. And it's like, well, guess what, none of this stuff is useful. Yeah, much of it is not useful in the real world. So

Maren Kate 16:56

totally, I mean, and then I guess back in the day, it's like he was If you were trying to get a trade, you go to a trade school, you'd learn the trade and then you would go directly to that. Yeah, it's really fascinating as everything changes and shifts, like how all the cracks in our education system are becoming more and more, more clear. So I love the things about cold emailing. I also just what have you, I guess some of the best hires you've ever made, and especially those who are are like internship style things. What have you seen the best candidates do like Are there any examples that pop out?

Matt Wilkerson 17:37

Yes, yeah. The best candidates I've seen for internships or just in general. They, it sounds simple, but they wrote an email that was personalized. Yeah. And it's, yeah, it just sounds so simple. But I mean, most of the most So the messages I get even on, on like Angel list where you can kind of write these messages me, people, they've got these cookie cutter

Maren Kate 18:08

message like any play. Yeah, I'm playing

Matt Wilkerson 18:09

I'm just like, I mean, no write Dear

Maren Kate 18:13

Sir Madam.

Matt Wilkerson 18:15

Just it's it really, there's the amount of time it does take to personalize is so worth it. It's so worth it and by the way, it's the amount of time it takes a personalized and find their email, figure out you know how to message them on LinkedIn or it's like, you know by, you know pay for LinkedIn in males it's totally worth it. It's worth it if you're a student especially because the the advantage you have as a student, especially Okay, let me tell you, if you're, if you're a student, or even if you're not a student, the advantage that you have, if you're, if you're just trying to get an internship is that you can start off by coming at it from a different angle. So you can start off by saying, look, I'd love to just get your advice. And this is where you're You, you know, you, you make people feel good. And you say, look, I was reading about XYZ that your group did or as reading that your company did this or you personally, it doesn't have to, you know, don't get too stalkerish. But you know, stuff that's just out there on it, you know, publicly, you can ask them for advice and say, Look, I'd really love to get your advice about something. And it doesn't have to necessarily be about asking for a job. That's one tactic. The other tactic is provide value. So email them something personal, and then do a few slides actually tell you the best intern who ended up getting a full time job offer after becoming an intern that I hired once he sent me this presentation that he had put together on our market and looking at a bunch of different things. And I was just so impressed with the thought that he put into this deck. I thought how can I not respond to him? I mean, it would be it would feel horrible then yeah, not responding. And getting at least on a call with this kid. I so and

Maren Kate 20:04

what's your offer? There's actually there's a it's not one of the cognitive it's something I forgot what it's called. But it's like if I, I have a better chance of getting something from you if I give you something first and whether you want it or not because then you're like I reciprocity, right?

Matt Wilkerson 20:27

Totally. Yes, exactly. Yeah. You want to give first always think about mindset. I get a lot of messages from people that are like, Hey, you know, I would really love to get your time, but they don't. And, and they don't lead by offering something even even if it's a call to his compliments, just complimenting someone first that gets them into the mode of wanting to be helpful.

Maren Kate 20:54

I think also in terms of especially as students um people are more willing to help like I have students that will email me and say, Hey, I'd love to chat with you about XYZ because I read this and would you be able to spare and I love when people say, Can you spare a specific amount of time? Could you spare 20 minutes, I'm like, totally, I can do that, especially if it's a student. Like, it's the whole idea of, you know, paying it forward. I think another thing is that I've seen because I love what you just said, with the intern that created this presentation, you're like, that's always impressive. One thing that I actually did years and years ago, when I was pitching, like my, my little web design shop that I ran out of college, is before had any customers, what I would do is I would pull the coffee and the design from a website or if they didn't have a website, I'd mock up in like it was whatever the janky version of Photoshop was. And then I would send it to them and say, Hey, I saw you didn't have a web presence you could like, we'd love to create one for you. Here's what one page could look like. And then we actually went more specific down the line. I was doing copywriting for Hospitality brands, I would literally pill a page from like a big hospitality brand, like a core, which is a multi billion dollar or used to be. And then I'd rewrite it. And I would publish a blog post that was a case study on a B, and then I would send that to a person there. And the amount of so it's like it, it I love things that are scalable, even in very personalized things like this. And I think if you're an intern, or anyone, no matter what you do for work, you should be building a portfolio. And if you if I see an intern who's created five or 10 presentations for companies similar to mine, and even if they anonymize the presentation, so anonymize where they've talked to, and they send a presentation to me and then they say Also, I've created some of this stuff for other people in your space. I would be blown away by that. It's It's them leveraging that work multiple times to.

Matt Wilkerson 23:06

And it was 100% it works so well because this is where you can actually marry your passion. With this. It's not like I think people hear this. They're like, Oh, you mean I've got to do all this like work free stuff and send it to people. It's exactly you find what you're passionate about. Find the people out there doing the things you're passionate about, and then start creating your own portfolio as and marry it with, with something that's relevant for them and start sending it out.

Maren Kate 23:34

Yeah, the portfolio idea is so important. I don't care if you're going to be an accountant. I don't care if you're going to be, you know, a product designer. It's like, at especially especially with remote because like at the end of the day with remote, it's all about results, right? Like, I don't care how long you sat at your desk, because that's not what I'm judging you on. I'm judging you on what you shipped pretty much what the results are. So any type of work, I think in The future, whatever it is, if you're doing it remote especially, you're going to need to figure out a way to show your work. And as a someone trying to get into a role early in their career just trying to break into a new field, if you can quantify and show your work and say, This is what I did at these last companies, or these last roles, or Heck, I haven't even had a job yet. But this is what I mocked up for XYZ, no matter whether it's finance or design or copywriting, like that will be so much more impressive than sending a resume or like, you know, to whom it may concern, blah, blah, blah.

Matt Wilkerson 24:36

Yeah, I, the, I think the big theme here that we're seeing is the shift towards entrepreneurship over, you know, kind of more accessible entrepreneur entrepreneurship over the last 10 to 15 years has been good in the sense that you're seeing more students take those kinds of initiatives because that's the idea here, right? It's this entrepreneurial mindset, the growth mindset that you hear everyone talk about, that isn't really taught in schools, right? Because schools are set up could be the antithesis of that it the school is set up to be about testing and leveled the level of evaluation and, and, you know, go to this class and get this grade. And the whole idea of taking ownership over these things gets sort of beaten out of you, right? Because you're told, well, you, you didn't get into this class, so you can't take it or you, you know, you didn't get this grade. So you're not going to be able to do this and, and that mindset, I think, makes a lot of students when you graduate think well, I got to go through the the job board properly, because that's what they said I have to do. And yeah, I followed. I followed what my professors and my school said, so I could get this grade. And then when you get in the real world, it's like actually, you just create your own path because there are no, you know, rules other than, you know what what had been passed. By law in this country, so that's what I think if the schools of the future are now, you know, within COVID, right, they're seeing a huge shift, they're having to go online, they're starting to get commoditized, they are going to have to be forced to either teach students really practical skills, like really entrepreneurial skills to fend for themselves, because the world does not stay the way you think it will, if anything is teaching us that now. And I think this generation will learn it better. That either teaching them real skills or helping them think about how to get to outcomes.

Maren Kate 26:38

Yeah, how to be how to be adaptable, and how to be just like, you know, flexible and roll with the punches. I think that's such an important thing. And you're right, you've got for eight years of schooling and you've been, you know, having to do the same type of thing. When you get on the other side of it. You assume that that's what you're supposed to do, but it's completely different.

Matt Wilkerson 26:59

Yeah. And the best education is real life. The best education is the real world. That's where you really learn. And that's what students are shielded from, for many years are shielded from the real world. And the schools that think about how to incorporate the real world, right? If it's co ops and apprenticeships and these sorts of things. And, and and loosen this restriction on, on having to everything around the grade and the GPA. That's where the best students I think of the future are going to come from.

Maren Kate 27:33

Absolutely. And I hope that that I hope that goes across the board to this been so great, man, thank you for your time. So just quick last two question. First of all, what is your favorite book or podcast from the last year and it doesn't have to be about professional just like, what what one Do you love the most?

Matt Wilkerson 27:53

So my, my favorite book, I would say it was a more recent one as well, but Kitchen confidential. Anthony Bourdain his first book, I finally read it. It took me a long time because I've always been a huge Anthony Bourdain fan. And after he, you know, passed away it was, I remember when it happened. I was thinking how could someone who I'm very happy with my life I don't, I've never say, Oh, I want to trade someone's life and he was the guy for a long time and say, Look, if I could trade life with someone, I would love his life. And so when he committed suicide that really kind of stopped you made me stop and say, Well, if if someone like that could suffer from depression, you know that it just says so much about what people what you think someone's life is. And yeah, I decided to read his book and I thought it was very entertaining. But you know, you can start to see his his back kind of dark side of him a little bit in the book comes threw, but I just thought it was an incredibly well written book.

Maren Kate 29:03

Awesome. I haven't heard that one before. I'll have to check it out. And lastly, how can people find more about you and Paragon one?

Matt Wilkerson 29:12

Sure, well Paragon one Our website is Paragon spelled pa ra ag o n and then one spelled o n e Paragon one calm and if anybody out there is just interested, you can either I mean I don't want to say I don't use Twitter that much. So I try to stay away from social media noise in some ways these days but you can just email me So Matt to Paragon one calm. Honestly, I don't mind getting emails from people that are super passionate about what we're doing.

Maren Kate 29:45

I love that and I really like I just wrote down. The idea is just like reiterating that be proactive and be passionate. It's like if you get an email or outbound cold outbound from someone and they're, they're showing that productivity and they're showing that passion people respect Well to that awesome Matt, thank you so much. Inde on air is brought to you by the first remote focused professional network and sponsored by going remote, the ultimate step by step guide to finding and landing a meaningful remote job in today's environment. Preorder today you'll get exclusive bonuses and access, just check out going remote that's going remote

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