What I read and found interesting this month, along with my thoughts on them.
The above is the result of the prompt “For these episode links (shared), can you extract their cover art and article covers, and give me a mock layout of their cover art with their titles for use as a composite LinkedIn banner that unifies these diverse podcast and article covers. Do not invent anything that is not true.” You can see the progression here and here!
Podcasts
“We will pair B-industries with an A-team”
Graham Weaver, Alpine on Invest Like The Best w Patrick O’Shaughnessy
Excellent episode. One that is about the strategy and tactics of operating a top-tier private equity fund (incidentally the most applied-to at HBS, Stanford GSB, Kellogg’s for its Alpine CEO program) as well as a playbook for your life (see Nine Lives below). I really liked the episode and Graham’s perspectives, and that led me to check out other podcasts where Graham Weaver has made an appearance. For those who liked his life playbook advice, the Lenny Rachitsky podcast where he appears is a good one.
Graham: Another belief that we have is the way that we’re really going to create alpha is through talent. That’s probably the foundation of Alpine: just we think that incredible leaders, CEOs, management teams are going to create amazing results. We’ll look at B industries that other people really don’t look at as much. But we’ve paired that with an A team. We found that to be just a great combination. We won’t overpay for the A industry. We’ll go down a little bit.
When we were in the recession we had all this time to kind of look back at our track record. The best deals that we did were always ones where we put in either us or someone just we to go run this business who knew nothing about the industry, but had these raw talent and also coachability to say, hey, I don’t know everything. So who do I learn from? Not this grizzled veteran that already knows everything about the industry, but I’m going to look at things differently and fresh. And by the way, I’m going to just run through walls. Those were our very, very best deals.
And so at one point we just said, let’s just do that every time. From this point forward, let’s just put our own team in a hundred percent of the time and we burn the boats. Brutal to burn those boats because bankers don’t sell companies that don’t have management teams.
So we had to rebuild an entire sourcing engine to do that. We had to change our brand in the market where the brand now, if you don’t want to continue, you call Alpine, as opposed to the other private equity firms that’ll back the founder. So it was really, really brutal to make that change. But, yeah, we made that change around 2010.
***
Patrick: You’ve told me before some of these incredible framing questions to expand the mind beyond incremental thinking into more blank-sheet thinking. One of the ones you told me that I liked best, that I’ve thought about a lot since, is imagine you have nine lives. You’re just going to do this life, what do you want to do in the second life and in the third life and really make it feel bigger, more expansive? Are there other questions that you found to be the most effective to get people to give you the real answer to what you’re trying to help them find, which is the thing that’s burning inside them?
Graham: Yeah. What’s cool about the nine lives exercise is I think people get really intimidated by saying, you got to find your passion. And I got one thing and they get in their head and I’m “Okay, let’s say you had nine.” They can rattle them off like right away: “Okay, I’d do this, I’d be a professor and I’d be a lawyer and I’d start this business. I’d do a nonprofit.” They could come up with them like right away. And then I’m like: “Good news, let’s do those. Yeah, good news. Your thing is in there somewhere.”
And then we try to take those nine and talk about which ones they have the most energy for. Who are they going to meet along the way? How are they going to grow? I mean, a great example is a student of mine. One of their lives is the thing they did before school. They were going to be a convertible bond salesperson. Life number three was run a business. And as they started learning, how are they going to grow and learn, the convertible bond one wasn’t as interesting.
Even though they were going to make more money doing that initially. You can dig into those nine lives and then it’s just a lower-stakes way to kind of get them to their something they’re passionate about. And the secret is you can have all nine at some point in your life, just not all at the same time.
Link to excerpts from the episode I found interesting.
‘A great investor can only impact a startup by 30%, while the right founder can 30x it%’
Jeremy Liew on the Icons Podcast, w Melanie Uno.
Jeremy Liew, who led rounds in unicorns such as Snap and Affirm, is no longer investing, having taken a step back to spend time with family and pursue hobbies like Tai Chi and contemporary dance. The podcast is a useful one to get a sense of his investing philosophy. Some nuggets:
- He believes that an investor or board member can only change the course of a company by about 30%, a great operator can at best make 3x difference, while the right founders can make 30x impact.
- The real challenge in venture is not telling good from bad as much as telling good from great. This requires a lot of time spent meeting thousands of founders / companies to be able to identify a one-in-a-thousand company. This comes not from reading and podcasts, as much as doing the reps and developing a sense of what makes a top 0.1% founder / company.
- To succeed in venture, and especially at the early stages of your career, you need to figure out your unique right to win. While you may not win every single time, you need to believe that you can win some of the time, even against the best. If you are competing against other good firms to win a deal, knowing your home ground advantage is crucial to making this happen – this could be network, domain expertise etc. (he mentions his younger colleague Nicole Quinn’s expertise in monetising celebrity-led brands such as Goop, The Honest Co), or having a unique point of view, expressed via writing, podcasts etc. You need to identify what sets you apart and makes you unique, as Nicole did, to succeed vs chasing every deal without a clear direction. For Jeremy what worked was his previous experience in consumer from his stint in Barry Diller’s IAC, and leveraging that to carve out a niche as a consumer investor, and compound the same.
Link to excerpts from the podcast episode I found interesting.
“I didn’t want to be rich. I didn’t want to be famous. I didn’t even want to be happy. I wanted to be great.”
David Senra on music producer and entrepreneur Jimmy Iovine in the Founders Podcast.
All excellence is born of suffering. This passage where David Senra describes the music production of Bruce Springsteen’s Born to Run is an apt example of how greatness descends from pain, and is coupled with it. Wonderful episode on music producer + entrepreneur Jimmy Iovine, describing his origin, evolution, philosophy, paired with lots of wonderful anecdotes such as this. The analogy between music producers enabling the artist’s vision to emerge, and VCs supporting founders is on point.
David Senra: I heard Jimmy say this quote that he heard from Springsteen, and then I immediately ordered the book. This is what Jimmy said. Bruce said something brilliant. He said, “I didn’t want to be rich. I didn’t want to be famous. I didn’t even want to be happy. I wanted to be great.”
Do you have any idea how many of the founders that you and I have studied on this podcast that that applies to? And so I went through Bruce Springsteen’s autobiography, and I wanted to see all the mentions of Jimmy Iovine in Springsteen’s autobiography. And I found this excellent quote on what Jimmy Iovine was like at this time in their life. And Bruce writes this line almost like he’s writing a song: “Jimmy Iovine, brilliant imposter, young studio dog with the fastest learning curve I’ve ever seen.”
So Bruce is applying relentless pressure on top of a young Jimmy. I mean, he says Jimmy would fall asleep at the soundboard. He was under so much pressure and so sleep-deprived, he almost quit. And then Bruce’s manager gave Jimmy some of the most important advice.
This is when Jimmy thought he couldn’t take it anymore and he tried to quit. And Jimmy said this is one of the most important things that anybody ever told him. He said, “Jimmy, stay in the fucking saddle. You are missing the big picture. What are we here for? We are here to help Bruce make the best record he can.”
“That’s the job. We’re not here to make you happy. We’re not here to make me happy. We’re here to contribute to Bruce’s project. And it is Bruce’s project.”
“If you go back in there and you say to Bruce, ‘I am here to support you. This is not about me. It’s about the album,’ you will have a friend for the rest of your life, and you have learned a lesson.” That is the big picture.
The idea to always stay focused on the big picture is the piece of advice that Jimmy would repeat and he would apply for the rest of his career. This is Jimmy’s key takeaway from that advice. He said, “You are there to help make their project better. And part of that is caring as much about their music as they do. I just said, if these people are allowing me in this room, I’m going to do as much as I can to be of service to them. That’s what it was built on.”
It’s funny, some of the best investors I know actually speak exactly like this and how they view the founders they work with. In fact, I was talking to Josh Kushner at Thrive, and he said almost this exact same thing to me. I’m going to read this back. And it’s really his view, or my interpretation of his view of the founders that he works for.
“You’re there to help make their project better. And part of that is caring as much about their music as they do. I just said, if these people are allowing me in this room, I’m going to do as much as I can to be of service to them. That is what it is built on.”
And so Jimmy doesn’t quit. Jimmy goes back in that room. He helps Bruce do whatever he can to make the best album he possibly can. And the result, the album they were working on is Bruce’s album Born to Run, which goes on to be the massive success.
Link to excerpts from the podcast episode I found interesting.
“Reading is grappling with the text, making connections….”
Ezra Klein on the How I Write podcast w David Perell
David Perell’s How I Write podcast is the The Paris Review interviews reimagined for the internet era. He interviews writers on their craft, as well as how they are leveraging AI in their work. This one with journalist and commentator Ezra Klein was fascinating. There are a couple of thoughts I take away from this. The first is how he visualises non-fiction book writing as a series of baton passing between different concepts, and how without extensive research, and having something to say, the book will just be largely empty rhetorical flourishes. The second was his thoughts on doing the work and not relying on AI summaries alone. When you do the work, when you read a book, the book is playing the role of a forcing function to make you think through the topics of the book. Hence when you read summaries instead of the book, you get what seems like the key message, but without the time spent internalising it, you will not take away anything meaningful from it.
Ezra: Having AI summarize a book or a paper for me is a disaster. It has no idea what I really wanted to know. It would not have made the connections I would have made.
…
I’m not saying AI can’t be useful or that it won’t be useful, but I think I’m pretty against shortcuts. You have to limit the amount of work you’re doing; you can’t read literally everything. But in some ways, I think it’s more dangerous to think you’ve read something that you haven’t than to not read it at all.
…
I wrote a piece about this a couple years back; it was called “Against the Matrix Theory of the Mind.” I think I used to conceptualize knowledge the way you see it in the movie The Matrix, where it’s like I wanted the port in the back of my mind that the little needle would go into. I had read John Rawls’s Political Liberalism. I thought that what you were doing was downloading information into your brain.
Now I think that what you are doing (when reading) is spending time grappling with the text, making connections. It will only happen through that process of grappling. So, the idea that you could speed run that, the idea that it could just be summarized for you…
Part of what is happening when you spend seven hours reading a book is you spend seven hours with your mind on this topic. The idea that O3 can summarize it for you, in addition to all this stuff you just will not have read, is it you didn’t have the engagement. It doesn’t impress itself upon you. It doesn’t change you. What knowledge is supposed to do is change you, and it changes you because you make connections to it.
…
I think that the time you spend with things is pretty important and a reason you get changed over time.
David: What I’m really taking from you here is actually what a book is isn’t just giving you a lot of information. It’s giving you a container to think about a narrowly defined scope of ideas. Part of reading the book is obviously downloading the information, but the other part is just the kind of rumination that happens in your brain in the process of consumption and just thinking about what it is that you’re reading.
Link to excerpts from the podcast episode I found interesting.
How quickly do you exit your first employee who doesn’t fit?
Charlie Songhurst on Invest Like The Best w Patrick O’Shaughnessy
This is an old episode, re-released recently. Charlie Songhurst was previously head of Corporate Strategy at Microsoft, and then turned (prolific) angel investor, and is now on the board of Meta. He covers a range of topics, but two stand out – a) why startups fail, and why we should study failure more b) how founders should recruit better. On the first he says that other than at the Seed to Series A where the lack of PMF kills, all other stages see failure due to the founder not able to leverage talent well, i.e., failure to achieve labour productivity. Hence the importance of hiring well, and this is a topic that Charlie dives into a at length covering such topics as the importance of early hires, why you should not panic hire, why the best founders quickly exit non-performers, and more. Good masterclass on talent management / recruiting.
Charlie: “Often one of the things that I see correlate very well with successes is how quickly they exit their first employee that doesn’t fit. And I think what that’s actually showing is are they willing enough to be disagreeable, to make the company what they want? And so the willingness to cross the chasm, and often you’re dealing with young founders, that’s a major inflection point.”
Link to excerpts from the episode I found interesting.
Additional Podcasts I liked
All Risk Is Creative podcast on Chris Nolan. Podcast series by management consultant turned content strategist Palash Kulkarni on “ risk and the creative act of risk-taking.” In this one, Palash covers Christopher Nolan’s evolution as a creator / director. Nothing new for Chris Nolan fans, but I found it an interesting listen. Gives you some glimpses into how Hollywood evaluates and takes creative risks.
Articles
Building a vertical saas co for the AI age: The EvolutionIQ story
Link to the article.
Highly recommended for vertical saas / vertical AI founders. The section in particular on focusing on guidance (vs automation), and designing for adoption (there are many other interesting passages) too was particularly interesting.
“The choice between automation and guidance is key for any AI product. Our decision early on was that we don’t want to get into automation. It’s the low-hanging fruit. It’s easier, it’s higher frequency — but it’s more competitive,” says Vykruta. “The internal teams might not be able to do it as well as an AI company, but they can do it reasonably well. The much harder piece is the tasks that cannot be automated entirely.”
Instead, the early EvolutionIQ product focused on helping claims adjusters make better decisions about where to spend their limited time. “A human expert might be dealing with managing 150 claims, or even thousands of claims at any given time. They need to decide where to spend their time. That’s hard for humans to do well,” says Vykruta. “Once they’re in the claim, that’s when you want the human expert to make the decisions — to pick up the phone, get more information from the doctor, call the employer, and so on.”
A key insight came from observing how other attempts at AI adoption in insurance had failed. “A lot of the clients we spoke with back then had an internal team building a model, or they were working with a ML vendor. And maybe these models worked, but then they gave the frontline examiner a spreadsheet with 20,000 rows that had some score in it,” says Vykruta. “A team would try to use it, but it didn’t really fit into their workday. They have to take an hour to go into the spreadsheet, look at stuff, and go back to their other UX and try to make sense of it.”
The EvolutionIQ team took a different approach. “To get adoption of complex AI, you need to have a beautiful interactive visual tool that people can work within. You can’t give them just a spreadsheet of scores and say, ‘Go run with this,'” says Vykruta. “We made a big investment from day one in not only developing the models, but also developing that UX they could log into and interact with.”
There are many other segments I found interesting including how they picked the space, product tradeoffs, picking the design partner and iterating, how they arrived at their enterprise sales motion and refined it for their space which has limited client universe. All fascinating.
From the perspective of an investor, I found the fact that they had a narrow TAM to begin with interesting. Wouldn’t have been an easy pick for the seed investor, First Round Capital.
Excerpts from the article I found particularly relevant, themed around key topics here.
Walking the high wire between tradition and innovation – Hunger Inc
Link to the article.
Long, really long, fascinating piece on the Hunger Inc Group of Restaurants, akin to the USHG of India. Looks at how the two founders came together, how they launched their first restaurant, The Bombay Canteen, as well as their subsequent properties O Pedro, Bombay Sweet Shop etc. Via the history, the piece also details how they approach the opening of a new restaurant by spending months eating local cuisine, talking to local food makers / home cooks, immersing themselves in local culture and tradition. Their guiding philosophy is that “unless you take the time you understand tradition, you’ll never be able to evolve it.” The privilege to innovate and experiment comes from having invested hours on getting the basics right.
The guiding principle of the company, one repeatedly hammered home for the team by Floyd, is that ‘unless you take the time you understand tradition, you’ll never be able to evolve it’. Girish had to first get the basics right before attempting to modernise mithai, which meant discarding his fancy thermometers and resetting his European pastry instincts.
…
Before opening (The Bombay Canteen), the team did what they’ve continued to do before launching any concept: immersive research. They traveled extensively across India, gathering not just recipes but context. Their approach wasn’t to visit established restaurants but to dive into homes, markets, and roadside eateries—places that are still strongholds of our food traditions. What they found was that ‘Indian cuisine’ wasn’t one thing but dozens, hundreds of micro-cuisines that varied widely in how they did things.
…
As has become customary to their process, in order to earn the right to have an opinion on the cuisine they wanted to showcase (Sajith: this was for O Pedro), the team embarked on an intensive 8-month culinary expedition. “I used to think that to make a restaurant menu it meant you went to college and learnt something, then you flipped through a few cookbooks, and then you’d draw up a menu based on what you knew. I didn’t know food could be researched like this,” admitted Hussain.
The entire team, from the chefs to the bartenders to the architects to the designers, made multiple trips to Goa. They conducted themselves like anthropologists, eating 8-9 meals a day at establishments ranging from fine dining restaurants to people’s homes to roadside vendors. They collected stories, recipes, and memories – documenting a culinary tradition that had been largely passed down orally rather than written in cookbooks. “I made friends with a million Goan aunties,” Hussain says. “Everywhere I went I begged them to share their recipes, to teach me how to cook. Now they’re all big supporters of ours.”
There is also an exploration of their philosophy of innovating on form or flavour at a time but never both. Sameer Seth, cofounder: “For any dish we either experiment with the form or the flavour, so there’s an element of surprise that makes things interesting, but it’s rooted in something familiar – a memory or an association that people can grab onto. If you stretch things too far on both form and flavour, you don’t give people anything to connect with. That’s when you start losing them.”
Managing the tension between tradition and innovation, thus, is at the heart of Hunger Inc, and their properties.
Excerpts from the article I found interesting, bunched around key themes here.
Transitioning from PLG to Enterprise: The dbtLabs story
Link to article.
This section on how @getdbt transitioned from a purely PLG motion to layering on enterprise is a fascinating one.
TLDR: GTM comprises your ICP, channel, and message. When you transition from PLG / bottom up to Enterprise / top down motion, naturally your ICP and channel also changes, but your messaging / proposition needs to change too, e.g., the enterprise may be multiple personas and are buying assurance as much as solution.
“Handy (founder) found product-market fit organically for dbt as an open-source tool mostly used by data practitioners and developers. But a few years into running a commercial business, he realized he had to build a growth curve all over again with C-suite data leaders.
“Even though we had an unbelievable amount of market pull, as we initially commercialized, it wasn’t easy for us to transform this open-source command line tool into a product that enterprises would pay a million dollars for,” says Handy.
…that product-led momentum couldn’t sustain the same growth curve within the enterprise for long. “Our first roughly $10 million in ARR was PLG-oriented, and so it felt like that would just continue to be true. But in data, that’s almost never true,” he says.
“When you have enough product-market fit, sometimes it allows you to get away with not being super tight on product marketing or sales motions. So around 2022, we went from this gigantic acceleration curve and overnight we realized, we have to sit at the adults’ table and figure things out real fast,” says Handy.
After the PLG flame started to fizzle, Handy turned his attention to layering on a sales-led motion for the cloud platform. “We had to focus our efforts on telling cohesive stories to senior data leaders. We had to have a very clear, explainable answer to the question, ‘Why should I use the commercial product and not the open-source product? And it had to be digestible by someone with a C in their title,” he says.
Handy’s answer: dbt Cloud can handle complex data for companies of every size.
“The longer people used dbt, the more complex their code became,” he says. “It was a problem for the most sophisticated dbt users, who were often at the largest companies. So there was a real opportunity for us to step in and solve that for them with dbt Cloud.”
To tell that story to enterprise customers, Handy relied on data, naturally. “At a user conference we presented a chart that showed the number of dbt projects that had a certain number of models in them — over 100, over 1,000, et cetera,” he says. “We watched that number climb and we knew as users ourselves, ‘Oh my God, trying to work in a dbt project with 5,000 models in it is challenging.’ So we started with that quantitative data point and asked folks in our community about their experiences with these very large, complex dbt projects, and validated that this was a pain in the ass without a cloud platform.”
How India’s government job exam system distorts the labour and education market
Link to the article.
Worth a read. Alex Tabarrok writes citing Kunal Mangal and Karthik Muralidharan how
1/ India’s public sector wages are v high
2/ As a result we have far fewer jobs than possible, limiting state capacity
3/ Because the few that make it come through a long and inefficient exam system that doesn’t teach real-world skills, it is leading to a lot of waste (specifically time of young men and women).
I have encouraged some of the founders I have met in edtech to start a college / degree where they offer a BA in General Studies (where the 3-4 yrs of teaching is broadly on the curriculum needed to crack the UPSC exam), or a Masters. This will make sure that the students don’t spend additional years preparing for the Govt exam. One other challenge is that post the exam there is a 1yr or longer waitline for the successful ones to be called for the job….that wastes time too.
“The two main criteria for a good erotic scene”
Link to article.
Fun, interesting read about the rise of intimacy coordinators in Hollywood and content producers for the big streaming sites. Intimacy coordinators are to love scenes, what choreographers are to dance scenes, but they also play the role of a liaison between the stars who have to reveal themselves and the directors / producers, making sure that nothing violates the dignity of those acting out a sex scene. Sort of a POSH coordinator + sex-scenes choreographer.
All right, now you want to know about the two criteria? Here you go:
In 1980, the director Francis Ford Coppola hired Constance Penley, a Berkeley Ph.D. candidate and an editor of a feminist film journal, as a research assistant on “One from the Heart,” a Vegas-set musical romance. The script included a sex scene, and Coppola asked Penley to identify what the best ones had in common. Coppola, Penley told me, “gave me an office at Zoetrope and a telex that I could use to call whomever I wanted and say, ‘Francis wants to know, What is the most erotic scene in film?’ ” Susan Sontag said that for her it was the wind blowing through Barbara Stanwyck’s hair at the end of “The Bitter Tea of General Yen.”
After reviewing hundreds of films, Penley gave Coppola a report that outlined two main criteria for a good erotic scene. First, the characters are not supposed to have sex. “There has to be some big difference between the two,” she said, one that makes their encounter unlikely. Second, one or both of the characters is “under threat of death.” As an example, Penley offered the sex scene between Linda Hamilton and Michael Biehn in “The Terminator,” in which the latter plays a man from 2029 who has travelled back in time to rescue Hamilton’s character from a cyborg assassin played by Arnold Schwarzenegger. “If you see it out of context, it’s O.K.,” she said. “But when you know he’s from the future and they’re being hunted, it’s really, really hot.”
A look back at the early days of venture investing in India
Link to article.
Athera Venture Partners, an Indian VC fund, took a look back at the early days of India’s venture fund industry. It carries interviews with three veterans of India’s venture industry, all of whom worked at TDICI (Technology Development Investment Corporation of India), India’s first VC fund.
“While searching for innovation from scientific institutions, I went to IITs, the National Chemical Laboratory and other research institutions but couldn’t make headway,” Deshmukh mentions. “I used to land up in Pune, Baroda and other cities, looked through the hotel’s directory, booked a cab and knocked on companies’ doors. They didn’t grasp exchanging equity for capital, and thought VC was another cheap lending instrument.”
“We were under pressure, even with a small fund of Rs 20 crore,” Deshmukh continued. “Telling people to part with equity, that we’d exit at some point, it took years for them to digest. It was an extensive education process through local industry and management associations besides meeting companies repeatedly.
“For example, I regularly travelled on the overnight Vadodara express from Bombay to Baroda to meet Dilip Sanghvi of Sun Pharmaceuticals – but took from 1989 to 1992 to get the deal done.”
I wonder what the venture investing equivalent of that is today; where you are literally begging someone to take your money.
Ecommerce shopping receipts as proof of residence
Link to article.
While the article is about the perilous state in which slum residents find themselves in, I was intrigued about the use of Flipkart and Meesho receipts to build up historical proof of residence and settlement as seen below.
Neha (pseudonym), 24, a resident of Delhi’s Shakur Basti, has just received a new pair of jeans from Meesho, her latest go-to shopping app. But before she even unfolds them, her focus shifts to the packaging they arrived in. With utmost care, she cuts out the invoice, smoothing its edges before tucking it beneath an envelope inside an old, metal trunk.
The trunk holds more than just miscellaneous papers; it contains the entire paper trail of her family’s existence in the city—ration cards, Aadhaar cards, her school certificates, and now, a growing stack of e-commerce receipts.
Neha doesn’t remember exactly when she started shopping online, but over the past few years, it has become routine. “At first, we ordered only things for the house—tiffin boxes, utensils, and a tarpaulin for the roof,” she recalled. “Gradually, we started buying clothes too.”
But while the items themselves are useful, it’s the invoices that matter most. For the past two years, Neha has meticulously saved every invoice from her online purchases, regardless of the product or its price. To her, these are not just receipts but proof—tangible evidence that she, her parents, and her two brothers exist in this jhuggi, in this lane, in this settlement.
“You never know when this might come in handy,” she told me, her voice carrying the uncertainty that has long been woven into the lives of informal settlement dwellers of the city. “No one knows when the bulldozer will come, when it’ll be our turn.”
“Through consistent training and legal workshops in slums, we have been advocating for the importance of saving crucial bills—electricity, water, and others,” said Abdul Shakeel, who leads the Basti Suraksha Manch. “While we organize camps and awareness drives, over time, people have found their own ways of archiving their lives through e-commerce platforms.”
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As acquiring legal entitlements from the state has become increasingly challenging, slum residents have developed their own ways to stake a claim to the city—one of them being e-commerce transactions.