Melissa Perri on Escaping The Software Build Trap

Episode Link: https://www.buzzsprout.com/126848/1452406

Youtube Channel Link: https://youtu.be/nswFpj2LrKE

Why did I do this show: I had been fascinated by how great software is made and what really makes great tech companies so much better at software than anyone else. This show came about as part of me trying to figure out how to think about technology.

What did I learn: I learned way too much and had to recognize what I learned only over the years following this interview. In a certain sense I did learn about software but I wasn’t ready to learn about it. I needed to try to build real software at a real software company to genuinely understand what Melissa taught me. So the thing I learned was that we can’t always learn the easy way.

What was my favorite part: This was the beginning of me figuring out that strategy is about constraints. Melissa’s book is entirely about how to effectively constrain an organization to make great things. It’s a very deep thing that I am still working to grasp!

Stan McChrystal on Risk and Leadership

Episode page: https://podcast.notunreasonable.com/126848/9951392-stan-mcchrystal-on-risk-and-leadership

Youtube link: https://youtu.be/QW5QrbBXaPk

Why did I do this show?

I’ve been thinking a lot about the relationship between leadership and risk. Then holy cow I learn that one of the most celebrated military leaders in a generation wrote a book about leadership disguised as a book about risk!? An incredible opportunity for me!

What did I learn?

I learned that the most distinguishing characteristic of Special Forces is (what I call) their moral clarity. An astounding and profound thing.

What was my favorite part?

Definitely Stan’s reaction to how President Bush judges leaders. Deeper than it seems!

Ty Sagalow on the Making of Lemonade

Episode Link: https://www.buzzsprout.com/126848/1515319

Youtube Channel Link: https://youtu.be/Qrmjl6HKotk

Why did I do this show? Lemonade is a legendary insuretech success and Ty was a co-founder. For those of us interested in insurance and technology this one was a no-brainer!

What did I learn? I learned that Ty was involved in a lot of insurance innovation in his career. The most common way new insurance products fail is not that they are underpriced and blow up a company, it’s that nobody gives a damn and sales are near-zero. Very important!

What was my favorite part? I loved digging into the superpowers of awesome engineering and product teams and Lemonade has those in spades!

Michael Tanzer on COVID predictions for Insurance

Episode Link:https://www.buzzsprout.com/126848/3092683

Youtube channel link: https://youtu.be/g51rXGioM7Q

Why did I do this show?

Michael is one of those finance people that I’ve envied ever since business school. Effortlessly seeing to the heart of all kinds of opportunities and ideas in investing. I have no idea how these people do this, they’re an awfully intimidating bunch. I still do not really know how to connect insurance prognostication to reasonable opinions about the path of the financial markets more generally so this is an attempt to analyze them all together. An experiment!

What did I learn? There are a whole series of interlinked price signals on insurance companies that I have zero visibility into. Spreads on certain preferred offerings against equity, say for Arch Capital? How interesting!

What was my favorite part? You’ll see that this is mostly an interview of me by Michael, actually. I can’t say it’s my favorite part to be interviewed but it’s always good to ‘cross the table’ and have a very smart person ask very good questions! Challenging stuff!

Christy Ford Chapin on the History of Health Insurance in America

Episode Link:https://www.buzzsprout.com/126848/2976040

Youtube channel link: https://youtu.be/WlnYHVFwKhM

Why did I do this show? I recorded this when I was working at a health insurance software startup and looking for a way to deeply study health insurance in the US. Boy did Christy deliver!

What did I learn? The most important insight in the book is nobody wanted the system we eventually got, except maybe the doctors. Insurers hate the idea of universal, compulsory insurance because it forces them to underwrite very difficult risks, that otherwise would never be able or want to buy insurance. Doctors knew that in other systems their ability to control patient care would be curtailed by a universal health care provider. Insurers offered the possibility of a fractured payor system that would not be able to dictate procedures.

What was my favorite part? My favorite part was actually getting to experience first hand Christy’s rapturous recital of all kinds of minutiae she uncovered as part of her research. It really takes a certain kind of talent to slot through all the materials she did to do her work. I was in awe of it.

Mary Hirschfeld on Aquinas and the Market

Episode Link: https://www.buzzsprout.com/126848/4376315

Youtube Channel Link: https://youtu.be/cxyA9SUvigE

Why did I do this show:

I’ve never been one that ‘into’ studying schools of moral thought but one thing I’ve noticed about the insurance business is that we do it all the time. For example, competitors don’t win by being good, they win by cheating and lacking in moral virtue. Success and failure both are moral failings in insurance.. how weird! This is one of my fundamental puzzles of insurance and so features in the podcast!

What did I learn:

There is a really dark side to Mary’s philosophy, as she says there is no such thing as societal moral progress, we’re really the same as we’ve always been. I don’t like this! But there is also a deeply uplifting side which is that for individuals moral progress is not just possible but essential to life. Surely our technology for helping the individual is aggregating over time like all tech?

What was my favorite part:

Learning that Aquinas is a kind of intellectual trump card in Catholic thought. If you can reliably demonstrate that you’re interpreting his philosophy with your position, you win!

Otakar Hubschmann on AI In Reinsurance

episode link: https://www.buzzsprout.com/126848/episodes/6184525

youtube channel link: https://youtu.be/w99YUTQAaLQ

Why did I do this show?

I have to admit, I’m a bit skeptical of AI in Reinsurance! I find Reinsurance to be very much about medium sized datasets and lots of human judgment, can we do anything better than that?

What did I learn?

One of the everpresent lessons in software is that there are always problems to solve. Every question is one of prioritization of resources and even relatively modest improvements in processes with big $$$ can be very valuable!

What was my favorite part?

Talking real about AI and reinsurance with someone who has legit experience!

Alex Lazarow on Frontier Startups

Episode Link:https://www.buzzsprout.com/126848/4424837

Youtube channel link: https://youtu.be/Axy-4ilhRKw

Why did I do this show?

Alex is an interesting guy! Not only from Canada but also trying to set out a logical structure for an alternate universe for how innovation happens in software. This is no easy task!

What did I learn?

Studying other cultures is studying alternate versions of one’s own universe. It’s always exciting to learn what works elsewhere so that we can bring those lessons home.

What was my favorite part?

That you can be from a small town in Canada and still come to understand startup ecosystems in Africa?!

Robert Hoekman on The Tao of User Experience

Episode Page: https://www.buzzsprout.com/126848/8328832-robert-hoekman-on-the-tao-of-user-experience

Youtube Link: https://youtu.be/-lyxd9E4lJM

Why did I do this show? When I joined the software world I was trying to figure out what made excellent software companies so much more excellent than… well everyone else because everyone makes software in their organization. The best answer I’ve come to is that amazing software companies have an exquisite understanding for what to build and why. That product skill, I think, is most heavily concentrated in the domain of product designers. Robert Hoekman is a designer extraordinaire and has so very much to teach us about building amazing things!

What was my favorite part? As I mentioned in my favorite clip from this podcast, he is relentless and unforgiving in the book. Behind it of course is an excellent guy!

What did I learn? There are deep and simple truths about great design that we can all say and even all believe. But unless we go through pain from not really, really knowing these truths we’ll never understand them.

Samir Shah on Innovating Capital

episode link: https://www.buzzsprout.com/126848/8171216-samir-shah-on-innovating-capital

youtube link: https://youtu.be/diERmzI7YSc

Why did I do this show? Inside the reinsurance world the idea of finding more ‘efficient’ capital carries an almost religious fervor. In my opinion there is a lot of silly thinking on the topic and Samir struck me as someone who combines idealism with a pragmatic and experienced flair. That is rare! I got the chance to take the gloves off and talk about all the things that really bother me on the topic!

What did I learn? learned about the underlying principle of Samir’s strategy, which I have to admit is one I agree with. It’s smaller and much more powerful than I had appreciated going into the conversation.

What was my favorite part? Oh, take on all manner of sloppy ideas about how capital really works in insurance and Samir and I were much more aligned than I had appreciated before. It was a fantastic conversation!