Founder's Journal Listener Mailbox

What's up, everyone. This is Alex Lieberman, co-founder, and Executive Chairman of Morning Brew. Welcome back to Founder’s 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.Today, we are going through the listener mailbox. Let's hop into it. 

Emails from listeners

So one of the amazing parts about building a media franchise and a community with hundreds of thousands of listeners is the ability to make an impact on so many people’s lives and the opportunity to build deep relationships with many of you. And in the last month, as we have just accumulated so many more listeners, I have gotten hundreds of listener emails ranging from a new founder who's looking for advice on fundraising, to a recent retiree that is resonating with my feeling of lacking direction. And in the last month, I've gotten hundreds of listener emails ranging from a new founder, looking for advice on fundraising to a recent retiree resonating with my feeling of directionless newness. First of all, if you haven't yet written into me, make today the day that you do it. Send me an email to alex@morningbrew.com, introduce yourself, and tell me why it is that you listened to the pod. Second, what I've realized is that there are so many insights packed into the emails from so many of you, and it would be a disservice to not share my reactions or my answers to several of them. So that's what we're going to do. I'm going to read a select few reader emails, react to them, and if it goes well, we'll do this again next month.

Email #1: Bringing fresh insight to a new venture

Starting with the first email. This is a response to the episode that we recently published called “Winning in Your Career as a Jack of All Trades.” And this episode was all about the value of being a generalist at a time when we are taught that specializing is the key to success. Here is a paraphrased version of what our listener had to say: “This podcast really struck a chord with me because it's something that I've really been struggling with. Often when someone wants to start a business, they'll end up disqualifying themselves because they have no experience, which is odd. There are plenty of people in the world with experience that are doing a terrible job. Instead of asking themselves, do I have experience in this industry? People should be asking themselves, what outside and unique insight do I bring to this industry? Andrew Carnegie, the oil magnet, started his career as a laborer. He dropped out of school at a young age. It was only when he taught himself to write that he started his business empire. He had no business education. Jeff Bezos worked for an investment bank. He quit his job in 1994 to start a virtual bookstore, which is now known as Amazon. He had no programming skills. Many entrepreneurs take what they've learned from their field and copy-paste their experience into their new business. This is problematic because it destroys their ability to look at things from a fresh perspective. It also means that they're subconsciously making the same mistakes as their previous employers. This is the paradox of expertise and of email.” Well, first of all, that was an incredible email and that was only part of it. It went on for a while, but I couldn't agree more with this listener. Expertise isn't necessarily a good or bad thing, but there are trade-offs to people who have a lot of expertise or have none of it. So let me just talk about my experience with Morning Brew. In the context of starting our company, it was incredibly valuable to not have expertise. Fresh eyes allowed us to think about things independently, rather than be stuck in thinking about how media has always been done. But on the flip side, my co-founder Austin and I saw the power of hiring for expertise, especially at the senior level, when we had gone so many years of being a very junior team with a bunch of 24 year olds. Expertise brings strategic thinking, and it also brings a process for planning for the future and building out an organization and a hiring roadmap. 

So this is how I think about it. If I am hiring someone without expertise, I am asking myself, how important is a learned skill for the person to succeed, maybe a skill that they don't have yet? And how growth-minded is this person to be able to work up the curve if they need to learn a new skill? On the flip side, if I'm hiring someone with expertise, I'm asking myself how important is fresh perspective and is this person capable of thinking differently despite being trained in a conventional manner for so many years? 

Email #2: What other Morning Brew products are in the offing? 

Okay, it's time for the second email. And it's a shorter one. I promise this listener said, “As you built Morning Brew, had you always planned to create a free product that would be monetized through advertising, or did you also plan some sort of hybrid that included a subscription product? If you had considered the hybrid option, would that have affected your decision to avoid raising venture capital money?” End of email. So if I'm being totally honest, in the early days of building Morning Brew, there wasn't really a long-term plan. This was a hobby. Sure, we had an investor deck that talked about us creating all of these different things, but in reality, we had this one newsletter and all we were focused on was making it as good as possible and focusing on turning it from being a hobby senior year of college that was a PDF into an actual business. And because we were first-time founders, we didn't have huge ambitions for the first several years of the business because we didn't know what being really ambitious as entrepreneurs looked like. As time has gone on, we have thought way more about monetizing our business in different ways, beyond just advertising, where our product is free to users and then companies pay to get in front of those users. And to your question, while subscription isn't on the immediate roadmap, there are two new business lines that we have placed a ton of focus on. The first is commerce and the second is education. So to speak to those for a second: Commerce very simply means Morning Brew selling products to its readers, its listeners, and its viewers. Those products could like look like apparel and merchandise, but it also could look like physical products where we launch new brands, whether that's journals or candles or desk toys. On the education side Morning Brew wants to basically build a complimentary product to the traditional MBA. It started with our eight week accelerator, which has gone incredibly well. And we're going to be building out Morning Brew Education as hopefully an eight figure business in the years to come. And regarding your question on fundraising, my guess is no, we still wouldn't have raised venture capital money. And the reason is by the time we were considering to launch other lines of business, whether it's education or commerce, our media business was already profitable enough to basically fund any of the new investments we wanted to make with our business. And my general rule of thumb is you should really only raise venture money when A) you need funds to finance your business that you don't have. This is common in a software business where it's high fixed costs in the beginning, and then marginal costs go down over time or B) when you're in a space where being first or largest matters a lot. So you need to raise a lot of money to spend a lot of money to get into first place. 

Email #3: Stay patient and enjoy the journey

Time for email number three: “Hey, Alex. Now that I'm 60 and still really active in my career, I've come to understand that the cycles I went through and different iterations of my career were an alchemy I couldn't replicate if I tried: one part ambition, one part inspiration, one part boredom, one part serendipity. The big moves I made that ended up making a huge difference sometimes were disguised as quote unquote short gigs or things I dabbled in that caught fire. It is okay for things to feel messy for awhile. In fact, if you tried to control it, you'll miss the point. I have absolute confidence that Morning Brew won't be your last fulfilling experience. Stay patient, follow your curiosity, give back, dabble, explore what's uncomfortable or hard. Most of all, enjoy the journey.” Honestly, I've never met this listener in my life, but I would take that last paragraph, print it out, and put it on my wall because it is just such a honestly wise take and how to think about career. And I'm going to talk about honestly, what a lot of this person said in the next email. But all I would say is they're spot on. Finding a way to enjoy the journey, finding a way to let my curiosity guide me. It's paid dividends thus far, and I need to continue to trust my gut. And also, I just love hearing from some of our older listeners who have had really long and successful careers because, you know, I would say typically this isn't the core listener of Founder’s Journal, but honestly, people have been working for 40 years who aren't retired yet and still are as motivated as they were 30 years ago. They just provide such experience and nuanced perspective that it's such a shortcut for learning. Right? Think about this person in an email, just summed up 40 years of career learning in four sentences. Like that is just an incredible shortcut and such an incredible privilege to have to get this email. So really appreciative for that one. 

The fourth and last email: “I recently read your piece about searching for direction. You're definitely not the only one to experience these thoughts and emotions. In fact, I recently experienced the same roller coaster when transitioning from being a therapist to entrepreneur, to working in a mental health technology startup. The way I see it, there are two factors at play here: First and foremost, you're back to exploration mode as opposed to execution mode, which is always difficult for strivers. Nevertheless, it is an essential part of the journey. Second of all, and perhaps more harmful in my opinion, is the factor of things never being enough and never being satisfied. Justin Kan from Twitch talks about this in his blog.” End of email. So there's three great points here that I just want to talk about quickly. The first is about the emotional roller coaster and searching for direction. And I think this naturally for me comes from always wanting to have a plan and wanting to have a clear idea of what my North Star is, which is such an interesting thing because I left the traditional path of going to business school, working in finance, going back to business school, starting a company. And so, by definition, I shouldn't, I should be comfortable with not having a plan, but I'd be lying if I said I felt comfortable with it right now. And in general, we, as people don't do well with ambiguity and not knowing where you want your career to go. And that is the definition of ambiguity. Second thing you talked about is this concept of exploration versus execution. How I visualize this concept is akin to having a metal detector at the beach. You spend a bunch of time scanning this,, the large expanse of the beach that you're on, and you're waiting for a signal that you should start going deeper when you hear that you've hit metal. The issue with the analogy, though, is that knowing when there's metal in a beach is very clear, but knowing when it's time to stop exploring and going super wide, and start executing, going very deep because you want to commit yourself to something I find is extremely difficult in your career because you have the huge trade-off of the other things you could be doing. And the question I continue to wrestle with is how do I know that I enjoy the thing that I'm doing and how many things can I commit myself to before I feel diluted? Third and finally is the point you make about being a striver while being satisfied. And you mentioned Justin Kan. He creates amazing content around this as well. And I think he felt the same feelings after building Twitch, selling Twitch, and moving onto his next thing. To me, this is the hardest challenge for any competitive careerist, not just entrepreneurs. How do you maintain the motivation to continue to grow and achieve while also having appreciation for the journey and what you have accomplished? I'm spending a ton of time thinking about this, because I think there are so many uber-successful people who start several unicorns and they end up getting to later in life and they never ended up feeling settled with all they have done. And as Jay Shetty told me recently, the best way to practice being settled and present is by practicing gratitude for yourself. So this is something that I'm doing far more of these days and something I plan to talk about on an upcoming episode. 

I want to hear from you

So to recap all of this, I freaking love my listeners. You all are the best, and there are hundreds of thousands of you. I want to share your questions and insights with the rest of this community. And if you enjoy this, I want to do this in the future. So like I said at the top, if you haven't yet introduced yourself, make sure to do it. Shoot me an email at alex@morningbrew.com. Tell me who you are and why you listen to Founder’s Journal. Also, if you haven't done so yet, make sure to pound the subscribe button, whether it's on Apple, Spotify, or the podcast player of your choice. Thanks again for listening, and I'll catch you next episode.