Every argument clarity score on this site is built from rows on this page. Each
question and answer was assessed with names hidden, the host's own answers included, on
four things from 1 to 5:
directness (does it answer the question asked), coherence (do the ideas follow),
precision (concrete details and clear references), compression (says a lot per word). The weighted
mix (30/30/25/15) is the exchange score. A person's published score averages their exchange
scores on raw tape only, at least 8 of them, shrunk toward the cohort mean.
Full method →
Answered raw tape
D 5 · C 5 · P 5 · Cm 5 5.00
Q Alright, let's talk about why personal holding companies are becoming a thing. What do you think is the opportunity here? Why is it taking off?
A Yeah, so I think there's just a number of different trends that we're seeing. Some are, like, Macro, cultural, and global trends. Others are trends specific to entrepreneurship and the business landscape. The first, which is like a global trend, is there's just increased emphasis on the importance of, like, lifestyle, balance, and health in a professional's life. And so I think it's very much in vogue now to be thinking about how you're taking care of yourself. We're in a golden age of entrepreneurship right now because the cost of failure of entrepreneurship has never been lower. It is easier than ever before to ideate or test ideas with platforms like Product Hunt or Kickstarter. It is easier or cheaper than ever before to actually run your business. You have an e-commerce business, you have Shopify. You have a newsletter business, you have Beehive. And so I think it's inviting more people to start businesses with this different image of what a great business is, and for a lot of people, that's a cash flowing asset that maybe does six to seven figures a year, gives you a great lifestyle, and maybe you Do that over and over and over rather than trying to swing for the fences with a ten billion dollar company that you have .1% chance of actually succeeding.
AI assessment note: “cash flowing asset that maybe does six to seven figures a year”
Answered raw tape
D 5 · C 5 · P 5 · Cm 5 5.00
Q Can you give us a timeline of how you get here?
A I dreamed of only one thing when I was growing up, and that was working on Wall Street. I went to college at the University of Michigan from 20 11 to 20 15. Studied business there, still on this path to have the world's greatest trader job ever. While I was at Michigan, week before my junior year, my dad passed away suddenly. He was 46 years old, died of a stroke, was in perfect health like me, and so, That feeling of obligation basically guided the next eight years of my life. It forced this perspective on me that every day could be our last, and we really should spend our time in a way that aligns with our values and fills us up. And so, I graduated from Michigan. I got the world's greatest trading job. I'm working on Wall Street, and I realize I'm not fulfilled in the slightest. While I was doing that, we had already started Morning Brew. And I was working on it on the side, and I realized I was so fired up by what I was doing from nine o'clock to midnight, far more fired up than what I was doing from six a.m. to nine o'clock. I quit my job when we had 30,000 subscribers. We had not made a dollar on the business, but I just had this sense of faith, and so did Austin, that we'd be able to figure out a way to make money as a business. So we sold the company in October of 2020 to Axel Springer. Almost six months later, I stepped down as CEO of the business, and that is Probably…
AI assessment note: “I went to college at the University of Michigan from 20 11 to 20 15.”
Answered raw tape
D 5 · C 5 · P 5 · Cm 4 4.85
Q You mentioned product market fit. How do you determine that, and how do you know when you've reached product market fit?
A It depends on the business that you're in. For Storyarb, I think of product market fit in two ways. One, as a percentage of, of our current clients, what percentage of our clients would recommend Storyarb to the people in their network, where their reputation is on the line, and I want that number to be at least 50%. The other number that I'm focused on is retention. Because again, I think the easiest part of this business Is getting customers. I think the hardest part of this business is keeping customers. And I've heard historically for ghostwriting agencies that when I talk to people who own ghostwriting agencies, they retain their average customer for like three to five months. That is like a scary short period of time. And so our goal is when we hit true product market fit, our average customer will have worked with us for on average, 10 months. And so those are the metrics we're focused on to hit that point. Where we feel like we can now scale our customer base now because clearly we're providing something that's super valuable to people.
AI assessment note: “For Storyarb, I think of product market fit in two ways.”
Answered raw tape
D 5 · C 5 · P 4 · Cm 4 4.60
Q Let's talk about the risks of a personal holding company. They're pretty sexy right now blowing up, but what do you think could be the downfall of that?
A Personal holding companies work well for people who understand what a personal holding company offers you, and it aligns with what you want to spend your time on. That's why I'm doing it. But the first big risk is dilution. It's lack of focus. Like, I want to get one business right before thinking about my next business. And so for Storyarb right now, We don't have product market fit in my mind. Until we have product market fit, I'm not going to launch another business. Once we have product market fit, I will launch a business. And so my whole thesis on this is go slow to be able to go fast. So launch a business, figure out how to hit product market fit. Hopefully that makes me better at launching a business and hitting product market fit faster the next time. And so each kind of iteration of launching and finding success with a business can happen faster and faster. But like, I don't also have a number in my head of like, oh, I need to be at 12 companies within the next three years. I would rather four successful businesses than 12 non-successful businesses. The second, when you have a personal holding company and you're the entrepreneur sitting at the top of it, you have to think of yourself as a product, meaning you are in service of the companies you launch and the CEOs that you bring on. And so, if you're a product, like any products, you have like value, you have value pr…
AI assessment note: “the first big risk is dilution. It's lack of focus.”
Answered raw tape
D 4 · C 5 · P 4 · Cm 4 4.30
Q A CEO runs each of the companies within your personal holding company. How do you find great CEOs?
A Basically, I look for a few qualities that I consider to be the unteachables. I look for someone who has an obsessive brain. I want someone who goes to sleep thinking about the business. I want someone waking up thinking about the business because it means they enjoy what they're doing so much. I want someone who's a great critical thinker. I want them to think about How are they informed by their previous experiences, but also how is this situation different and how do they need to behave differently? I want someone who's value aligned with me. Like I want someone who is high integrity, strong communicator, like the things that really matter, no matter what business you're working in. And the final piece is a great work ethic. Every day of the week, I'd bet on someone who is less talented, but has more humility and self-awareness because I believe If they also have good work ethic, like they will just grit their way to a higher ceiling, and they will also always be willing and have the humility to call out their blind spots, but I really think it's almost impossible to teach good work ethic, and so I need that in a site CEO that I bring on.
AI assessment note: “Basically, I look for a few qualities that I consider to be the unteachables.”
Partly raw tape
D 3 · C 4 · P 4 · Cm 3 3.55
Q Alright, so you got this one successful business. Now you're thinking of new ideas. Can you tell me how you, Approach new ideas, and how do you validate them?
A First of all, the best way to think of business ideas is to never just sit on a couch thinking of business ideas. That is the worst way to do it, right? Be a magnet for problems, so be incredible at finding and hoarding people's problems, and then thinking about what are novel solutions for solving those problems. If I wanted to launch another business today, I would, but I want to focus with StoryArm first, so if anyone wants to steal one of these ideas, they can. The first idea is what I call workflow automation agency. I think the next big one will be basically like notion or air table or different forms of automation agencies using these no code tools like Zapier and make as well as using AI and offshore talent. And I think every business you want to finding people working on manual tasks that can be automated or outsourced. So if I was to build my next business in the hold code, it would be that. I think there's so much opportunity to build it, so your audience should feel free to steal the idea and take it and build it themselves.
AI assessment note: “Be a magnet for problems, so be incredible at finding and hoarding people's problems”
