In this classic episode of the Founders Journal, Alex Lieberman—co‑founder and executive chairman of Morning Brew—shares four hiring stories that illustrate the principles he uses when evaluating candidates, especially friends or acquaintances. He first explains why the show is republishing classic episodes for new listeners. He then recounts hiring Neil, the managing editor, who impressed him by teaching a 45‑minute lesson on the Battle of Gettysburg, demonstrating deep curiosity and the ability to "show" knowledge rather than merely "tell" it. Next, he describes Toby Howell, the voice behind Morning Brew’s Twitter account, who got on the team by constantly engaging with the company on social media and delivering a full‑sample newsletter before being asked—an example of "permissionless apprenticeship" and "will‑your‑way‑into‑the‑ecosystem". He also mentions Oswin, the original Founders Journal producer, who similarly offered free blog‑post conversions and social clips. Finally, he details a senior leader who first worked as a freelancer, built a 6‑12‑month strategic roadmap, and proved value before a full‑time hire, underscoring the benefit of a freelance trial and the necessity for senior hires to present a long‑term vision. Alex distills four key hiring lessons: (1) prioritize candidates who show curiosity and skill rather than just claim it; (2) look for those who will their way into your ecosystem and practice permissionless apprenticeship; (3) consider a freelance‑to‑full‑time path as a risk‑mitigating test; and (4) require senior candidates to articulate a strategic plan and hiring roadmap. He ends by inviting listeners to share their own standout interview experiences via email or Twitter.
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What's up, everyone? This is Alex Lieberman, co-founder and executive chairman of Morning Brew. Welcome back to Founders Journal, my personal audio diary, where I give you, the business builder, the tools you need to think better in order to build better, whether that's building a business, a team, or a new product. So I need to share an update, and that is for the next little while, we're going to be republishing classic episodes of Founders Journal. 2 reasons. One, because these are really good episodes that I spend a lot of time on. And with so many new listeners to the show, it's very likely you haven't heard some of these older episodes, and I think you'll benefit from them. Second, I'm spending a ton of time thinking about how to evolve this show so that we can make it as good as humanly possible for the next generation of builders and entrepreneurs. And with that, I would love your help as I dream up the future of this show. So once you've listened, shoot me an email to alex@morningbrew.com and don't hold back. Any feedback, recommendations, ideas? I want to hear it all, and I want to have it help me inform where this show is going. That's the update. Now, time for the episode. In today's classic episode, originally published on February 3rd, 2021, I present things you should consider before working with a friend or a family member. Let's hop into it. Over the last 6 years, I've probably personally interviewed at least 500 people. I've had some good interviews. I've had some not good interviews, and I've had a few interviews that have blown my mind. I want to share a few of the incredible ones so you know what a great interview and candidate looks like as you go about hiring or interviewing. The first story is about our current managing editor at Morning Brew, who at the time we hired as our second writer ever. So This had to be in early 2017. We had 3 people on our team. We had my co-founder Austin, we had myself, and we had our first writer. And our first writer was working probably 13 hours a day. So we needed more capacity and support for our writer. And so we were looking for a second writer. And the second writer, now our managing editor, Neil, he demonstrated a level of curiosity and and a level of creativity that I've never seen before in my life. It is what makes him so effective at writing and leading the Morning Brew team. And one of the best ways that he stood out in the interview process was by showing us how curious and capable he was versus telling us. And this is exactly how it went down. I was interviewing him in a conference room of an accelerator in New York City. And I'm going to be honest with you, up until this point, I didn't know how I felt about him as a candidate. He didn't seem super excited. He didn't have a lot of variance in his tone, so I couldn't tell if he was really happy to be talking to us or not. But I asked him a simple question that changed everything. I said, what are you really passionate about outside of writing and outside of Morning Brew? And he goes, U.S. history. I studied history in college and I just love thinking about and studying our past. And so I said to him, okay, I want you to teach me something about U.S. history. For the next 45 minutes of the conversation, Neil broke down the Battle of Gettysburg better than any textbook could have. And to me, this was awesome for 2 reasons. One is I love learning, and I now knew more about Battle of Gettysburg than I ever had in my life. But 2, Neal proved to me through his own experience and his own acquisition of knowledge that he had gone further down the rabbit hole on the Battle of Gettysburg than 99.9% of society. And what that told me was, in the context of Morning Brew and our role, Neal is going to be someone who, if he takes interest in this role, is going to go deeper than anyone else can. So while the context was different— U.S. history, the Battle of Gettysburg— It showed his way of thinking, and it showed that he's not like 99% of other people who they say they are curious. They say they go down the rabbit hole, but only go, say, 10% below the surface. He goes all the way down. The second lesson that I learned from Neil is I said to him, we need someone who's creative, we need someone who's witty, and we need someone who's thoughtful. How are you those things? And rather than Neil just saying to me that, you know, I've always been a creative person. I did creative writing in school, or I, you know, am considered the wittiest person in my friend group. He actually shared a video with us.
Call your friends. Save the date. My parents gave me a nice surprise. Son, it's time. We're going to get you circumcised.
And the video he shared with us was this YouTube video that had been uploaded a few years prior. Tim interviewing for the Brew, and it was an a cappella group that he was part of at the University of Maryland when he— where he went to school. And the a cappella group was singing a song for an audience. The song was called Chop It Off, and the song was about circumcision. Neil was not only a singer in the a cappella group, but he had produced the lyrics to the song. It was one of the funniest, most clever songs I had ever heard in my life. And so from that point on, after seeing this video of Neil producing Chop It Off and him knowing more about the Battle of Gettysburg than most people could ever imagine in their life, I knew he was the person for the role. So the lessons from our experience with Neil was make sure people show you rather than tell you just how intellectually curious they are, and also make them show you examples of how they've applied the technical skills you need for the role in practice or in life. After the break, I want to give you the story behind how we hired the voice behind Morning Brew's Twitter account. So a quick break. Let's hop back into it. So I told you the story of Neal, our managing editor, and how he showed us his curiosity and his creativity. Now, the second story is about Toby Howell, who is currently the voice behind Morning Brew's super popular Twitter account. And Toby is someone that just showed us his relentless interest in Morning Brew well before he applied for a job at the Brew. He started interacting daily with members of the Morning Brew team on Twitter. He would reply to my tweets on Twitter. He would retweet what Austin was saying. And what I learned from this experience is Toby was going to do anything necessary to leverage the tools at his disposal to get in front of the key decision makers at Morning Brew. And clearly what he knew to himself is in a world of social media where you have access to anyone, he had this incredible opportunity to start creating content on Twitter and to start interacting with people on Twitter so that he could get on our radar and actually just show his abilities as a social media creator. The second thing that he did is what I like to call permissionless apprenticeship. And I didn't come up with this term. It's a term that's been used for a while. But basically what permissionless apprenticeship means is you do work related to your skill set for the company you want to work for without asking. Basically, you deliver work and then it starts a conversation. And so what Toby did was he actually wrote up a sample newsletter for us because he wanted to apply to be a newsletter writer at Morning Brew. So rather than saying he is a great writer, rather than waiting for us to give him a prompt to write about, he just literally created an entire Morning Brew from scratch, sent it to us, and then asked if he could have a conversation. And I've had this very similar experience actually with the original producer of Founders Journal. The original producer back— called a year and a half ago. His name's Oswin. And the way he applied for Founders Journal was actually not by telling me he was applying. He was a listener of the show. He took all of the past episodes of the show. He turned them into blog posts, and his suggestion was to turn Founders Journal episodes into a blog so that we could generate traffic for the podcast. He just sent me all of the blog posts for free. He also sent me social media clips and he just said, hey, I hope you like these. I love the show. I just wanted to do this for you. And when I saw this, I was like, damn, there's no way I'm not going to start a conversation with this guy. He just did so much free work, so much smart free work, We got to see if he's interested in continuing to do this for us. And so the lesson from Toby's experience or from Oswin's experience is to look for candidates that will will their way into your ecosystem because they want a job so badly. And then they also show you how badly they want it with permissionless apprenticeship. The final special interview process is actually a more recent hire at Morning Brew, someone who is a senior leader at the company. And basically what this person did was they created an entire roadmap of what they wanted to do over the next 6 to 12 months at the company. And they also proved themselves as a candidate before ever becoming full-time in the company. Here's what I mean by it. We had met this candidate, the senior leader, through our network, and they had just left their previous job. But they didn't join Morning Brew full time to start. They started as a freelancer where they helped us with thinking about our sales process to grow our sales team, to help us think about how we price our advertisements, to get our financials in place. They did this all as a freelancer, as a part-time employee. And what this basically gave the ability for everyone to do is understand, is this person a good fit? They got to prove their value to the company while getting paid. And they also got to get a feel for themselves. Is Morning Brew right for them and is the company headed in the right direction? And so what we learned from this process is, one, if you can go from a freelance relationship to a full-time relationship, it can be a huge unlock and risk mitigator for a company. And also, when you're talking to a senior employee like this, not just this person, but any senior employee, you should have the expectation in an interview process that they show you their long-term strategic plan. So where they want their organization to go and who they need to hire to make that happen. It's not going to be perfect because they're not spending all day in the company yet. But the number one thing for senior leaders is to set a strategic vision and know how they're going to execute on that vision with people. If they can't do that, you're going to be in trouble. And so these are 3 interview processes in more than 500 interviews that have absolutely blown me away and taught me a few key lessons of what to look for in candidates. First, look for people who show versus tell their curiosity and skill set. Second, look for people who will their way into your ecosystem and practice permissionless apprenticeship. Third, there is a ton of value in working with someone in a freelance capacity first before hiring them full time, if you can pull it off. And fourth, if you're hiring a senior person, it is a must. that they walk you through their initial long-term plan and hiring roadmap thoughts in the interview process. Now, I'd love to hear from you. For managers listening to this episode, what is an incredible interview that stands out to you and why does it stand out? For non-managers, what is an interview process that you feel like you've crushed in your career and what about it made it such a killer experience for you? Send an email to alex@morningbrew.com or DM me on Twitter @BusinessBarista with your thoughts.
