The Ledger
Every statement that passed quotation and attribution checks. Mix any filter with any other: certainty 1/5, debate potential 5/5, or both at once.
why aren't all 248 resolved? a statement only gets an assessment when the public record can support or contradict it. opinions and what-ifs never can, and 0 checkable ones are still open, waiting for their date. predictions held up or didn't; assertions are supported or contradicted. on every card: ▮▮▮▮▮ certainty · ▮▮▮▮▮ debate potential. speakers are clickable
Rief: Outgrown executives cause worse organizational bloat than outright bad hires
“There's two types of mishiring, and I think people usually think about the first that I'll give you, but it's the second that really kills you. The first is you just mess up. You hire a senior exec, you know within four to six months of the wrong person hopefu…”
Lieberman: Fear-based extrinsic motivation is exceptionally effective
“Being driven from a place of fear is exceptionally effective.”
Alex Lieberman: More founders regret selling too late than too early
“Far more entrepreneurs regret selling their business too late than entrepreneurs who regret selling their business too early.”
Lieberman: Superfan referrals drove Morning Brew to 4.5 million subscribers
“We have four and a half million subscribers, but if you were to ask me what has been the number one growth driver for Morning Brew, I wouldn't say it's our paid marketing that we did on Facebook. I wouldn't say that it's cross promotions with other newsletters…”
Lieberman: Scaling Morning Brew to 300 employees in 18 months forced layoffs
“I remember when I would tell people that Morning Brew post-acquisition, we scaled from 50 employees in October of twenty-twenty to 300 employees in a year and a half. People were like, oh my god, that is the most amazing thing, and then when I give them the pu…”
Lieberman: Highly connected campus leaders make the worst brand ambassadors
“The people we thought would do best as ambassadors, the people who were most connected in their student body, who were in five different clubs, who were You know, student body president. They were actually the worst ambassadors because they were spread so thin…”
Lieberman: Staying in the CEO role too long was his biggest mistake
“I think the biggest mistake was probably actually staying in the CEO role too long.”
Lieberman: Happiness plummeted after selling Morning Brew and stepping down as CEO
“Deal was October of twenty-twenty. Moved out of the role in April of twenty-twenty-one. My happiness actually went down a lot.”
Rief: Morning Brew would have failed if started intentionally as a business
“We didn't intend for it to be a business. And if we did, and we thought about it as a business in 2015, I think it would have failed. We would have made long, short term decisions to make a little money here or there, but because of the side project, we didn't…”
Rief: The study claiming happiness caps at a $70k salary is wrong
“I think there's like that whole 70,000 dollar salary you know, study that people are happier at 70,000 dollars. I don't think that's true. I think I am happier”
Lieberman: Startups should hire a strong HR leader early
“Biggest lesson, or one of the biggest lessons I learned is you can't hire HR early enough, or like, you can, but I would just say, like, when we hired HR, it was too late. It's one of those things that you're never gonna feel like it's the right time, but if y…”
Lieberman: Work-life balance does not exist when building a company
“I don't really believe in work-life balance in general when you're building a company. There isn't this clear delineation of church and state or work and personal life”
Lieberman: Layoff conversations should be 90% manager talking
“A layoff conversation should be 90% manager talking, 10% employee. There, unfortunately, is very little upside to making it a more balanced conversation.”
Reference calls test the referee's caliber more than the candidate's
“I have found that reference calls are generally not incredibly enlightening, but they're almost as much a Barometer of the quality of the reference as the person that you're doing the reference call for. Meaning if you believe that people are a reflection of t…”
Lieberman: Quitting a hopeless business prevents costly wheel-spinning for founders
“I don't think that it is inherently a bad thing to think about throwing in the towel on a business, because if you don't do that, and you're working on a business that has no hope of working out, you can end up spinning your wheels way longer than you should, …”
Lieberman: Fear of financial instability was Morning Brew's primary driver
“It is incredible how much motivation can come from the fear of not having enough money, and the fear of, kind of, Your family members or the people that you love deeply, their quote unquote financial safety. And so that was, I would say, the biggest driver of …”
Lieberman: Selling an A+ product beats being an A+ seller
“Being a B plus seller of an A plus product is a hell of a lot better than being an A plus seller of a B plus product.”
Lieberman admits co-founder Austin Rief was a better stage-two CEO
“I believe that Austin was a better stage two CEO at the time than I was.”
Lieberman: Scaling requires shifting CEO role from product-market fit to org-building
“Chapter two of building a business, which goes from the job of being a CEO is achieving product market fit to the job of being a CEO is Building a company. Like, actually building an organization that allows you to grow beyond a single product and be around fo…”
Lieberman: Austin Rief took over CEO-level operating duties from 2019 to 2020
“From 2019 to through 20 20, Austin had very much taken on the responsibilities that were necessary for a CEO Who was now in kind of the company building mode and no longer in the startup building mode.”
Alex Lieberman: Stepping down as CEO was harder than selling Morning Brew
“And I would actually say, very interestingly, the Move out of the CEO role was far more difficult and far more emotion and identity provoking than was the decision to sell the business.”
Lieberman: Hub-and-Spoke Marketing Yields Far More Leverage than 1-on-1 Sales
“So a hub is something, a digital channel or an in real life channel that gives you leveraged access to a lot of spokes. Spokes are your, the ideal customer you want to get in front of. Again, we didn't think about it in this way at the time, but it's how I thi…”
Lieberman: Newsletters Can Start Monetizing Around 10,000 Subscribers
“On today's episode, I'm going to talk about how we got from zero subscribers when we first started Morning Brew to 10,000 subscribers, which I would say is roughly the point at which you can actually start making money off an email newsletter.”
Lieberman: Elite Student Leaders Make Poor Brand Ambassadors Due to Overcommitment
“The first time we tried an ambassador program, we went for quality over quantity. So we took a bunch of ambassador applications. We only accepted like 10 ambassadors, and they were the people who were like the best students, involved in the most business clubs…”
Lieberman: The Best Ambassador Programs Automate Entry and Reward Top Performers
“And so ultimately, where we shook out is the best possible ambassador program is this hybrid we did, where we let in
Like, we made it a quantity game, so we let in every ambassador, but a lot of it was automated until they proved that they provided good work a…”
Waiting for full clarity before starting a business guarantees failure
“As they think about taking any sort of quote unquote leap of faith into building something is it never feels clear. It never feels clean. It always feels messy. And when you make the decision, whether it's to start a business, whether it's to go all in on a bu…”
Startups should maintain evergreen job listings for their core competency roles
“Every company has its core competency, and for its core competency, it has one role that Is most important to deliver on that core competency. At Beehive, it's a full stack engineer. At Morning Brew, it is, it was a newsletter writer. Now it's, you know, write…”
Founders should hire future entrepreneurs for their first 10 startup roles
“The first 10 employees in a startup. You should be able to look at them and say to yourself, I think this person will do incredible work for us for a number of years, but ultimately I could see them starting a company of their own.”
Lieberman: Selling Morning Brew brought no ecstasy compared to early building years
“Everyone thinks that when you sell your company, you feel like you're on top of the world. When you get money wired into your bank account after a sale, you must feel this ecstasy. And I felt none of those things. And when I think about the times that I felt m…”
Ads in Competing Newsletters Yielded Morning Brew's Best Paid Subscribers
“It's always been the highest quality channel for paid acquisition has been spending on ads in other email newsletters, because at least it is a behavior that someone already has.”
Lieberman: Morning Brew succeeded because there was nothing original about it
“If I look back at my one big career win, Morning Brew, there's really nothing original about it. Business news has existed since the 1700 and email has been around since the 19 seventies. And that is exactly why it worked. We did something that we already knew…”
Lieberman: Morning Brew Succeeded by Verifying Industry Dogmas Firsthand
“I think what allowed us to be different is that we didn't assume any quote-unquote industry truth to actually be true until we verified it for ourselves.”
Lieberman: Time freedom after Morning Brew did not bring happiness
“Even though I had freedom of time after stepping out of the CEO role for Morning Brew, I wasn't happy. Because I didn't have a sense of purpose, and more importantly, I didn't feel like I was growing.”
Lieberman: Entrepreneurship transitions should be calculated risks rather than leaps of faith
“The way I think about it is people talk about this leap of faith, but I actually think if you build a Business effectively, or if you mitigate risk effectively, if you treat something as a side hustle before it becomes a full-time job, you should be looking at…”
Lieberman: Founders probably will not enjoy every stage of business
“You don't have to like every stage of business, and in fact, you probably aren't going to like every stage of business.”
Lieberman: Career success requires spending 80% of time on core strengths
“In career, you want to stack the deck in your favor, and the way you stack the deck in your favor is you have self-awareness of the two or three things that you're really good at, and you work your way into a job or a position where 80% of your time is spent o…”
Lieberman: Morning Brew only raised $750,000 in total outside capital
“I guess we weren't technically bootstrapped because we raised, like, 750 K, but from family and friends that was kind of all we ever raised.”
Lieberman: Most confident angel investments come from backing former employees
“I would say I'm a highly mediocre angel investor, but the check I feel most confident in is the Morning Brew employee who I watched for five years and literally no due diligence went into my conversation with him. I just gave him a check.”
Lieberman: Leaving a Startup Causes Loss of Motivation, Identity, and Confidence
“And what I've noticed is basically every founder who leaves their business Whether it's successful, not successful, whether they've sold the business or not sold the business, they basically go through the same exact journey, and I'm going to describe the jour…”
Lieberman: News media succeeds only via analysis, niches, or edutainment
“There are three ways to win in news today. So in the news business, there's basically three formulas that work. The first is world-class analysis. So it's not about breaking the story. It's about having the best take And point of view on the story, that's some…”
Lieberman: Media value comes from saving time and making audiences look smart
“I think that saving people time and making them appear smart to their peers is a huge value add, and so that was just something that made me think back to the early days of morning brew of why I think it provided value for people.”
Lieberman: Media Franchises Win by Adapting Proven Concepts Into New Form Factors
“62nd Startup very much just brings an old idea, which is Shark Tank. You know, founders pitching judges in front of an audience. It takes that idea and it just brings that idea to a new form factor, which is short form social. And then even if you think back t…”
Denk: Early startup roles offer unique impact over corporate jobs
“You could be one of 20,000 people at Deloitte in that exact same role, or you could be one of one, the only person building what you're building at Morning Brew and make a real difference.”
Internal benchmarking causes founders to hire 2x instead of 10x executives
“The more you use a reference point from your own business, the more you open yourself to possibly making the mistake of hiring someone who maybe is one or two X better versus the 10 to 15 X better because you don't truly have an understanding of what really se…”
Lieberman admits 60% of his motivation for Morning Brew was money and status
“I would say 70% of my motivation or not 70, 60% of my motivation for morning brew was financially driven. Financially or status driven.”
Morning Brew built its famous referral program with a $500 Upwork developer
“There was software that was out there at the time that we could have paid for to just use for Morning Brew's referral program, but instead, we found a developer on Upwork who was in Ohio, and we paid him 500 dollars to build Morning Brew's referral program.”
Lieberman: Morning Brew's free student legal work cost 3x to fix later
“So we had all of our original, like, operating agreement, our tax number, all those filings done for free, but it ended up being really shoddy work. So the first lawyer that we ended up getting after graduating from college. Basically had to redo everything. A…”
Top business minds often possess chronically paranoid brains
“I find that some of the most impressive business minds have chronically paranoid brains, and in general, I wouldn't call Justin a paranoid person, but I mean this trait in a good way. When I was talking to Justin about his business, one of the things he mentio…”