What are your interests?
Select categories to help us recommend content for you.
Let's Go!
Close queue History
Play full episodes to fill your queue.
Fathom beta logo
   
Invest Like the Best with Patrick O'Shaughnessy

Invest Like the Best with Patrick O'Shaughnessy

25 Episodes • By Colossus | Investing & Business Podcasts • joincolossus.com/
Conversations with the best investors and business leaders in the world. We explore their ideas, methods, and stories to help you better invest your time and money. Hear stock market and boardroom insights you can't find anywhere else. If you're a professional investor, CEO, entrepreneur, or busines ...more
Technology Investing Management
Invest Like the Best with Patrick O'Shaughnessy
Invest Like the Best with Patrick O'Shaughnessy
@investlikethebest
mute button
Carl Kawaja - Dealing with Regime Change - [Invest Like the Best, EP.314]
My guest this week is Carl Kawaja. It’s the second t... more
Jan 31 2023 1h 12m
Planting Seeds for Long-Term Success
Chapter 1 3 mins
[First question] What the market feels like to him today
Chapter 2 3 mins
The pros and cons of the cost of capital and experimentation
Chapter 3 5 mins
Things we can learn from Oil & Gas stocks and resource commodities in general
Chapter 4 5 mins
Pulling apart the key lessons from Berkshire’s purchases of IBM and Apple
Chapter 5 5 mins
The practical implications of wanting to land more soft-wins in investing that aren’t apparent out of the gate
Chapter 6 5 mins
How he approaches and considers products and product cycles writ large
Chapter 7 2 mins
The Systems Bible
Chapter 8 5 mins
Thoughts about making money from value based strategies
Chapter 9 4 mins
His methodology to go about finding the next diamond in the rough
Chapter 10 2 mins
A New Innings
Chapter 11 3 mins
The Arc of Boxing ; Lessons from Muhammad Ali fighting Cleveland Williams
Chapter 12 5 mins
Someone he thinks is an exemplar in both business and the world
Chapter 13 5 mins
Don’t Sleep There Are Snakes
Chapter 14 7 mins
The role fossil fuels play in the energy transition and the current regime change
Chapter 15 4 mins
What we can learn from uncontroversial transitions in the past
Like
Clip
Share
Transcript
More
Play Full
mute button
Daryl Morey - Systems Thinking in Sports - [Invest Like the Best, EP.313]
My guest this week is Daryl Morey, who is President ... more
Jan 24 2023 1h 3m
The Concentration of Resources in Sports
Chapter 1 6 mins
[First question] The basic principles of sports and what makes for a great sport
Chapter 2 3 mins
How resource concentration influences outcomes in various sports
Chapter 3 3 mins
The degree of certainty in predicting sports outcomes based on existing data
Chapter 4 2 mins
Using the concept of KPIs to optimize for certain characteristics to win games
Chapter 5 2 mins
Training teams on specific systems and plays versus leveraging individual talent
Chapter 6 2 mins
Why superstar athletes are key to success in basketball
Chapter 7 1 min
Dealing with constant expected value calculations to appease stakeholders
Chapter 8 3 mins
Building the organization’s back office to find talented athletes
Chapter 9 5 mins
How he and other GMs make organization-level decisions
Chapter 10 2 mins
Why he’s involved with basketball as opposed to other sports
Chapter 11 1 min
How he uses his frameworks to figure out systems outside of mainstream sports
Chapter 12 4 mins
Problems with the rules and economic factors of professional soccer
Chapter 13 1 min
Suggestions to mitigate huge point spreads that make viewers disinterested
Chapter 14 2 mins
Trends he’s observed in the worlds of music, movies, and books
Chapter 15 2 mins
His perspective on developing one’s own career path
Chapter 16 1 min
How challenges in his youth benefited him in the long run
Chapter 17 1 min
The person he would call for advice if he was stuck in a foreign prison
Chapter 18 1 min
His emphasis on first principles and why he supports free speech
Chapter 19 4 mins
Takeaways from a Harvard negotiation class he took
Chapter 20 1 min
The power of refining the terms and definitions of a deal post-negotiation
Chapter 21 2 mins
The four people in the world that intrigue him most
Chapter 22 1 min
The kindest thing anyone has ever done for him
Like
Clip
Share
Transcript
More
Play Full
mute button
Miles Grimshaw - The DNA of Software Companies - [Invest Like the Best, EP.312]
My guest today is Miles Grimshaw. Miles is in his ea... more
Jan 17 2023 1h 10m
Who Are the Customers?
Chapter 1 2 mins
[First question] His notion of the investor as a biologist or a physicist
Chapter 2 2 mins
Why he seeks out new companies with unique business models
Chapter 3 4 mins
How his investments are based on present and future needs in the market
Chapter 4 1 min
Evaluating the genetics of a nascent or small company
Chapter 5 3 mins
The half-life of information as it flows through a company or platform
Chapter 6 3 mins
Unpacking how software companies can survive re-evaluation periods
Chapter 7 4 mins
The power of environment creation and facilitation
Chapter 8 34 sec
The importance of user conferences
Chapter 9 4 mins
A company’s potential for a differentiated second act as a sign of good genes
Chapter 10 2 mins
Product quality, timing, and reinvention in tech startups
Chapter 11 4 mins
Why it’s crucial for companies to avoid copying their heroes
Chapter 12 3 mins
Breaking down market perspective on pure API companies
Chapter 13 2 mins
His views on software targeted to vertical versus horizontal markets
Chapter 14 3 mins
Carefully leveraging relationships with core customers
Chapter 15 2 mins
Operational lessons from his experience with the companies he’s invested in
Chapter 16 45 sec
His maxim that software development is as much an art as a science
Chapter 17 1 min
His idea of a product magician in the software industry
Chapter 18 6 mins
Effects of new products and categories at the forefront of the space
Chapter 19 3 mins
How software founders should prepare for 2023
Chapter 20 2 mins
How both market structure and product shape the genetics of a business
Chapter 21 2 mins
The challenge of pricing and packaging for SaaS companies
Chapter 22 59 sec
Cardinal sins in software investing
Chapter 23 2 mins
The kindest thing anyone has ever done for him
Like
Clip
Share
Transcript
More
Play Full
mute button
John Fio - Creating Magic for Consumers - [Invest Like the Best, EP.311]
My guest today is John Fiorentino. John is a produc... more
Jan 10 2023 1h 21m
IP in the Consumer Space
Chapter 1 6 mins
[First question] The amazing story behind Gravity Blanket
Chapter 2 4 mins
What he’s learned about positioning relative to product
Chapter 3 2 mins
How fundamental truths drive creativity in commerce
Chapter 4 3 mins
Real-world examples of magic as he defines it
Chapter 5 5 mins
The investability of consumer businesses from his perspective
Chapter 6 2 mins
His contrarian thoughts on venture-backed startups
Chapter 7 10 mins
How unique personalities create compelling IP and monetize it
Chapter 8 6 mins
The fine line between creative power and self-destruction for brand founders
Chapter 9 3 mins
The importance of consumer business goals being larger than oneself
Chapter 10 4 mins
The story of the Moon Pals weighted stuffed animals
Chapter 11 4 mins
How investors undervalue IP and mythology
Chapter 12 3 mins
Leveraging uniqueness as a founder to boost your brand power
Chapter 13 4 mins
His eye-opening experience working on Justin Bieber’s team
Chapter 14 3 mins
How he identifies potential magic-makers and enables them
Chapter 15 2 mins
An odd commonality between high-level successful people
Chapter 16 3 mins
Whether or not one could map out their own archetype framework
Chapter 17 2 mins
The dangers of focusing on one’s own persona and image as the product
Chapter 18 3 mins
The kindest thing anyone has ever done for him
Like
Clip
Share
Transcript
More
Play Full
mute button
Amjad Masad - The Future of Software Creation - [Invest Like the Best, EP.310]
My guest today is Amjad Masad. Amjad is the founder... more
Jan 3 2023 1h
Design Tools Impact Organizations
Chapter 1 3 mins
[First question] The Steve Jobs black-pill
Chapter 2 3 mins
Speculation on the near future of programming
Chapter 3 1 min
Potential convergence of simple software and coding tools
Chapter 4 1 min
What an IDE is and how it works
Chapter 5 1 min
The definition of REPL and the role of Replit in the space
Chapter 6 5 mins
Decreasing friction in a programming environment using primitives
Chapter 7 3 mins
Real-world effects of Replit’s low-friction design
Chapter 8 7 mins
His perspective on new coding and AI technologies
Chapter 9 2 mins
Promises and limitations of the user-friendly programming movement
Chapter 10 6 mins
The dynamic nature of IDE technology and its challenges
Chapter 11 4 mins
How he’s priming his team to react to new technologies like the upcoming GPT-4
Chapter 12 3 mins
Recommended skills and training for the AI world of the future
Chapter 13 4 mins
The impact of IDE and AI tech innovations on existing tech giants
Chapter 14 2 mins
His mixed but optimistic views on the trajectory of AI
Chapter 15 2 mins
Recommendations for the curious listener without a programming background
Chapter 16 1 min
The role of smartphones in the IDE movement
Chapter 17 2 mins
The kindest thing anyone has ever done for him
Like
Clip
Share
Transcript
More
Play Full
mute button
Rebecca Lynn - Finding Your Customers - [Invest Like the Best, EP.309]
My guest this week is Rebecca Lynn. Rebecca co-found... more
Dec 27 2022 51m
The Sins of the Survey
Chapter 1 2 mins
[First question] What she’d do a great job teaching if she could teach a singular 401 level course
Chapter 2 49 sec
Defining what the umbrella concept is
Chapter 3 5 mins
What about her career at P&G applies most to the kinds of companies she spends her time with now
Chapter 4 3 mins
What types of questions she asks to help someone building a product understand their marketing angle
Chapter 5 3 mins
The top three things people do wrong when running a survey in tactics or strategy
Chapter 6 1 min
Categories of questions where surveys are always helpful and effective
Chapter 7 7 mins
What the Go-To-Market Council is and what it does
Chapter 8 2 mins
The ways that most funnels are commonly broken
Chapter 9 2 mins
Defining great positioning and what it accomplishes
Chapter 10 1 min
How her knowledge and ideas most impacted the way she built Canvas
Chapter 11 4 mins
Lessons learned about the world of digital health and the quantified self
Chapter 12 3 mins
The base level attributes that most indicate investment potential when she’s investing in a company
Chapter 13 3 mins
The shifts in the world that most have her attention today
Chapter 14 3 mins
What has her worried systemically about venture investing
Chapter 15 1 min
The kindest thing anyone has ever done for her
Like
Clip
Share
Transcript
More
Play Full
mute button
Michael Mauboussin - Sharpening Investor & Executive Toolkits - [Invest Like the Best, EP.308]
My guest this week is Michael Mauboussin. Many of yo... more
Dec 20 2022 1h 6m
Investment Tools
Chapter 1 2 mins
[First question] Overview of Michael’s recent research on market share
Chapter 2 2 mins
Market share dynamics in modern history
Chapter 3 3 mins
How market share data is useful for investors
Chapter 4 2 mins
Investing in early breakout companies from low-concentration markets
Chapter 5 54 sec
Surprises from his recent research project
Chapter 6 3 mins
Using the value stick for stakeholder satisfaction
Chapter 7 4 mins
Examples of value creation using the value stick
Chapter 8 8 mins
Market power in relation to markups and willingness to pay
Chapter 9 11 mins
Identifying a company’s real ROIC numbers
Chapter 10 3 mins
How important absolute ROIC is when picking investments
Chapter 11 7 mins
Research on capital generation and allocation trends
Chapter 12 5 mins
Characteristics of great capital allocation strategies
Chapter 13 3 mins
Surprises in the market since his deep-dive research
Chapter 14 3 mins
Artificial intelligence and other sources of disruptive innovation
Like
Clip
Share
Transcript
More
Play Full
mute button
Jeremiah Lowin: Explaining the New AI Paradigm - [Invest Like the Best, EP.307]
My guest this week is Jeremiah Lowin. Jeremiah has b... more
Dec 13 2022 1h
A History of Modern Machine Learning
Chapter 1 2 mins
[First question] What a pre-trained transformer is
Chapter 2 3 mins
What latent representation means in the context of AI models
Chapter 3 1 min
Models using math to interpret input data and generate images accurately
Chapter 4 2 mins
Whether or not understanding AI complexity in light of the results they arrive at will become a black box scenario
Chapter 5 3 mins
A high level history of the companies involved in generative AI
Chapter 6 3 mins
The precursory technology that makes generative AI art possible
Chapter 7 5 mins
What people are doing to improve AI models in between versions
Chapter 8 3 mins
Things that are literally happening during AI training
Chapter 9 3 mins
The power dynamics and barriers to entry for building AI models
Chapter 10 2 mins
Whether or not AI models might one day function as a utility like electricity
Chapter 11 4 mins
Coding using GitHub Copilot and what it’s felt like to use it
Chapter 12 4 mins
How he’d approach starting an AI company from scratch
Chapter 13 5 mins
Developing this technology beyond general and into specific use cases
Chapter 14 3 mins
The secret sauce for defensibility in the AI model space
Chapter 15 3 mins
What he’s watching more closely as the story unfolds
Chapter 16 4 mins
Whether or not he thinks that these toolkits will eventually learn how to use other systems like Unreal Engine on our behalf
Like
Clip
Share
Transcript
More
Play Full
mute button
Bill Lenehan: Investing in Commercial Real Estate - [Invest Like the Best, EP.306]
My guest today is Bill Lenehan. Bill is the CEO of F... more
Dec 6 2022 1h 16m
Sam'sell on Real Estate Investing.
Chapter 1 5 mins
[First question] Recent increases in mortgage rates and a frozen housing market
Chapter 2 4 mins
Projected real estate trends over the next decade
Chapter 3 3 mins
How a company’s ROI can be more consistent with backing from a real estate firm
Chapter 4 3 mins
Risk-return rate and risk exposure in real estate compared to other asset classes
Chapter 5 2 mins
The skills, traits, and circumstances that make a top-level real estate investor
Chapter 6 10 mins
Stand-out learnings from his time at Farallon Capital Management
Chapter 7 6 mins
The value of shopping malls and offices in a post-COVID, e-commerce US
Chapter 8 3 mins
Pros and cons of different types of real estate investments, including REITs
Chapter 9 2 mins
The impact of climate change on the real estate market
Chapter 10 5 mins
The role of modern technology in investing and in real estate infrastructure
Chapter 11 3 mins
Hard costs of building and renovating for the future
Chapter 12 2 mins
How hard costs and supply levels impact rates of return and housing costs
Chapter 13 4 mins
How the retail industry is adapting to consumer trends
Chapter 14 2 mins
Why retailers need to adapt to a changing economy and how they’ll do it
Chapter 15 2 mins
The relative magnitude of change in today’s real estate market
Chapter 16 2 mins
The role health and wellness plays in real estate and finance
Chapter 17 2 mins
What it feels like to be investing in 2022
Chapter 18 4 mins
The kindest thing anyone has ever done for him
Like
Clip
Share
Transcript
More
Play Full
mute button
Ron Howard and Brian Grazer - Box Office Business - [Invest Like the Best, EP.305]
Today I’m joined by two Hollywood greats, Ron Howard... more
Nov 29 2022 52m
Keeping the Creative Spark Alive.
Chapter 1 5 mins
[First question] The value of trust and how Ron built it up over time with Brian
Chapter 2 6 mins
The spark that allowed Brian to trust and work with Ron
Chapter 3 1 min
Ray Stark calling Brian and threatening him over their mermaid movie
Chapter 4 3 mins
Keeping their creative spark alive as their business scaled and matured
Chapter 5 3 mins
Principals like the universality concept that they return to most commonly
Chapter 6 2 mins
Seemingly bottomless wells of inspiration that they both pull from
Chapter 7 3 mins
Curiosity precedes innovation and the curiosity conversations Brian has
Chapter 8 2 mins
The pitch format Brian uses to try and secure a guest for a curiosity talk
Chapter 9 1 min
The role of engaging with conversations or ideas Brian disagrees with
Chapter 10 3 mins
How curiosity shapes the nitty gritty of Ron’s directing and producing
Chapter 11 2 mins
The biggest mistakes they’ve come across that people make telling stories
Chapter 12 3 mins
Pinpointing the defining moments of their careers outside of the obvious wins
Chapter 13 2 mins
Thoughts about how the industry has changed across their careers
Chapter 14 2 mins
How they’ve gotten better at taking a project from nothing to the finish line
Chapter 15 3 mins
The kindest things anyone has ever done for them
Like
Clip
Share
Transcript
More
Play Full
mute button
Shane Battier - The No-Stats All-Star - [Invest Like the Best, EP.304]
Today’s episode is a special one, in a format that m... more
Nov 22 2022 54m
The NoStent All Star
Chapter 1 4 mins
[First question] What people measure in basketball, what matters when it comes to winning, and why he was called a replaceable cog in the No-Stats All-Star
Chapter 2 3 mins
Some of the plays that impact the overall points during a basketball game
Chapter 3 2 mins
The role that preparation and understanding game analytics plays in the ability to do something different and succeed at it
Chapter 4 1 min
The power of curiosity and obsessing over details
Chapter 5 4 mins
Embracing his role and how being a role player applies to life outside of the court
Chapter 6 2 mins
Where his obsession for winning and being a good team mate comes from
Chapter 7 5 mins
Some of the things great leaders and coaches did to inspire him
Chapter 8 5 mins
An overview of the four types of teams and fundamental aspects of them
Chapter 9 2 mins
What a person can do to elevate their team and make it a winning one
Chapter 10 3 mins
Antifragility and the letter Shane wrote for Ravi when Amazon bought Whole Foods
Chapter 11 3 mins
Riding the thin line between winning a championship and being irrelevant
Chapter 12 1 min
How to get everyone rallied around a long-term shared mission effectively
Chapter 13 5 mins
Finding a No-Stats All-Star in a company and what to look for in one
Chapter 14 2 mins
The kindest thing anyone has ever done for him
Like
Clip
Share
Transcript
More
Play Full
mute button
Parker Conrad - Building a Compound Company - [Invest Like the Best, EP.303]
My guest today is Parker Conrad, co-founder and CEO ... more
Nov 15 2022 1h
Benefits of Being the Customer
Chapter 1 9 mins
Compound Startups
Chapter 2 7 mins
Ripple Lane vs. Salesforce
Chapter 3 8 mins
The Advantages of a Compound Startup
Chapter 4 5 mins
Advantages of Rippling in Commoditized Markets
Chapter 5 5 mins
Rippleaine
Chapter 6 7 mins
Good Communication in a Fast Growing Business
Chapter 7 7 mins
The Productivity Paradox
Chapter 8 6 mins
The Compound Business
Like
Clip
Share
Transcript
More
Play Full
mute button
Bob Elliott - A Macro Tour - [Invest Like the Best, EP.302]
My guest today is Bob Elliott, the CEO and CIO of U... more
Nov 8 2022 1h 20m
Gold and Commodities Investments
Chapter 1 4 mins
[First question] The Economic Organization of a POW Camp and key lessons one can learn from the paper
Chapter 2 2 mins
The way that supply and demand clears a price and how that plays into his thinking about investing across asset classes
Chapter 3 1 min
Whether or not he has a generalized investing worldview or framework
Chapter 4 3 mins
Deciding on what data is signal and matters most when analyzing markets
Chapter 5 4 mins
A crash course on easy money and tight money regimes and the implications of both in a macro environment
Chapter 6 3 mins
The rise and role of inflation and what should be done about it
Chapter 7 6 mins
What the next couple of years will look like if we draw lessons from history
Chapter 8 4 mins
Why gold could ever belong in someone's portfolio when it doesn’t produce or yield anything back to the investor
Chapter 9 5 mins
Supply and demand constraints and the state of the housing market today
Chapter 10 5 mins
What might happen in future labor markets given our current macro environment
Chapter 11 5 mins
Currencies, energy, geopolitics, and what he’s most focused on globally
Chapter 12 3 mins
What movements in the charts are worrying him the most
Chapter 13 6 mins
The original “All Weather” portfolio and what one would look like if he built it today
Chapter 14 5 mins
How his career has taught him to find talented individuals who might deliver alpha
Chapter 15 5 mins
Lessons learned from early-stage and venture investing and thoughts on that world now
Chapter 16 3 mins
Why there hasn’t been an iconic early-stage technology investing firm driven by systematic strategies
Chapter 17 3 mins
The kindest thing anyone has ever done for him
Like
Clip
Share
Transcript
More
Play Full
mute button
Kirsten Green - Investing in Consumer Change - [Invest Like the Best, EP.301]
My guest today is Kirsten Green, founder and managin... more
Nov 1 2022 1h 9m
Market Headwinds and Tailwinds
Chapter 1 4 mins
[First question] The insights gleaned from studying consumers in the modern era
Chapter 2 2 mins
Whether or not the shift in consumer behavior is similar to a platform shift like mobile
Chapter 3 1 min
Which of her hypothesis going into the research was proven most wrong
Chapter 4 2 mins
The leading persona archetype that drives consumer spending
Chapter 5 2 mins
Thoughts about her investing focus after doing all of this research
Chapter 6 2 mins
How much the digital world is good and bad for community
Chapter 7 2 mins
Positive and negative impacts digital access has on children
Chapter 8 8 mins
The investing criteria that she and her firm have developed for founders and business models they find desirable
Chapter 9 2 mins
An example of the middle of the spectrum between tailwinds and headwinds that may result in them passing on a business
Chapter 10 3 mins
The beachhead problem for entry points, encouraging good focus and entry point selection, and who’s done it well
Chapter 11 4 mins
The history of the consumer of how they buy and sell and where the shifts in power have been
Chapter 12 3 mins
Other interesting trends she’s seeing in the seller empowerment era
Chapter 13 3 mins
How different her investing models are for linear product businesses
Chapter 14 3 mins
Frameworks she’s developed for evaluating a brand early on
Chapter 15 3 mins
The most defining moment in Forerunner’s history and the hardest lesson she’s had to learn
Chapter 16 50 sec
Ways she’s fostered and mentored young investors at Forerunner
Chapter 17 45 sec
What the most underappreciated thing is today about the consumer
Chapter 18 1 min
User and customer development strategies that work well for early stage products
Chapter 19 3 mins
Three businesses young investors should study to educate themselves on great consumer businesses; Shoe Dog
Chapter 20 5 mins
Where they find the companies Forerunner tends to invest in, and how to build and effective deal flow pipeline
Chapter 21 4 mins
The kindest thing anyone has ever done for her
Like
Clip
Share
Transcript
More
Play Full
mute button
Jason Droege - Building Uber Eats - [Invest Like the Best, EP.300]
My guest today is Jason Droege, a venture partner at... more
Oct 25 2022 1h 4m
Tony Shoe on Being Available
Chapter 1 4 mins
[First question] What it was like at a high level building Uber Eats
Chapter 2 2 mins
How he would structure entrepreneurial incentives on a platform like Uber for a new leader or team attempting to build on top of it
Chapter 3 4 mins
What he learned about selecting competitive frontiers and mistakes made while building Uber Eats
Chapter 4 2 mins
Things that Uber Eats got most right that he’s proud of
Chapter 5 2 mins
Constructive mistakes that taught him a lot from his time with Uber Eats
Chapter 6 2 mins
What made India such a competitive environment
Chapter 7 3 mins
Building a business with an uncertain end state of unit economics
Chapter 8 1 min
What improved the most in his playbook for launching in a new city
Chapter 9 1 min
Defining what best means in this competitive sector
Chapter 10 3 mins
Dealing with suppliers in different categories and finding an ideal balance
Chapter 11 1 min
When monogamy between the buyer and supplier matters and when it doesn’t in a marketplace
Chapter 12 2 mins
Other attributes of a marketplace he’d pay special attention to as an investor given what he’s learned building one
Chapter 13 1 min
Defining what founder market fit is and being “fingertippy”
Chapter 14 2 mins
His views on the relationships between leaders of businesses and their cultures
Chapter 15 1 min
Why Uber believed in him more than he did
Chapter 16 2 mins
What he learned about marketing to suppliers specifically
Chapter 17 1 min
Find new businesses by looking for areas that technology hasn’t yet affected
Chapter 18 2 mins
Differing views he has on the concept of failure
Chapter 19 1 min
Thoughts about ideas versus execution and the relative importance of the two
Chapter 20 2 mins
Effectively measuring opportunity cost and using it in decision making
Chapter 21 5 mins
What it’s like being inside of a consumer business that people have so many opinions about
Chapter 22 2 mins
How he would describe the landscape and state of the market he was in from a higher viewpoint today
Chapter 23 1 min
The most interesting things he’s learned from his time as a partner at Benchmark
Chapter 24 3 mins
The kindest thing anyone has ever done for him
Like
Clip
Share
Transcript
More
Play Full
mute button
Paul Orfalea - It’s About the Money - [Invest Like the Best, EP.299]
My guest today is Paul Orfalea. Paul founded Kinkos,... more
Oct 18 2022 46m
Wall Street Did Something Stupid.
Chapter 1 1 min
[First question] What it was like to be a very bad student in highschool
Chapter 2 39 sec
When he first realized he was unemployable
Chapter 3 1 min
The origin story of the very first Kinko’s
Chapter 4 43 sec
What the ideal progression of an entrepreneur is in his mind
Chapter 5 55 sec
Recognizing real customer problems and what he enjoys most about sales
Chapter 6 1 min
Finding what has worked well in each Kinko’s and coaching managers
Chapter 7 1 min
Something he found that a manager was doing that blew him away
Chapter 8 1 min
Getting messages from his brain to everyone else in the Kinko’s network
Chapter 9 1 min
The difference of working on and not in the business
Chapter 10 34 sec
What he got better at when it came to managing people
Chapter 11 43 sec
Why a good salesperson will sell you broke
Chapter 12 26 sec
Disagreeableness as a positive characteristic for people in business
Chapter 13 27 sec
Whether or not candor is different from disagreeableness
Chapter 14 2 mins
Why he teaches, what he teaches, and his teaching style
Chapter 15 1 min
Explaining the Federal Reserve in two minutes
Chapter 16 18 sec
What students most commonly want from him
Chapter 17 1 min
Whether or not making yourself inaccessible as a leader is good for promoting a self-starter attitude amongst team members
Chapter 18 18 sec
The story about tearing down a sign that was antagonistic to a customer
Chapter 19 32 sec
The role of anger in his career and something he’s worked on over time
Chapter 20 1 min
Where Kinko’s falls on the spectrum of bad to great businesses
Chapter 21 58 sec
Characteristics he’d look for in founders to back a business early
Chapter 22 1 min
Qualities of a business he’d cultivate more or less if he could start over
Chapter 23 23 sec
Lessons learned about using the word employee
Chapter 24 38 sec
His strategy for where to go next once he had his original concept
Chapter 25 23 sec
The most clever marketing strategy he ever deployed or designed
Chapter 26 44 sec
Learning to spread the glory instead of the money
Chapter 27 1 min
The state of entrepreneurship today compared to when he started
Chapter 28 51 sec
How he instilled frugality and the saving mentality in the business
Chapter 29 52 sec
What motivated him across his career
Chapter 30 58 sec
Why being in it for the money seems odd in today’s lens
Chapter 31 16 sec
Who he most admired or most admires today
Chapter 32 16 sec
Let My People Go Surfing: The Education of a Reluctant Businessman
Chapter 33 33 sec
Preserving the alignment of integrity and action
Chapter 34 1 min
What it felt like to sell a business he’d worked so hard on
Chapter 35 2 mins
How good he is naturally with numbers and math being dyslexic
Chapter 36 47 sec
Defining success as having your adult children want to hang out with you and what stood out about his parents to him
Chapter 37 28 sec
His parents’ impression of him while he was building Kinko’s
Chapter 38 1 min
What has his interest and keeps his interest most
Chapter 39 51 sec
The most interesting person he’s ever worked with at Kinko’s
Chapter 40 35 sec
What he would have done differently if he started from scratch
Chapter 41 1 min
Something that is most underappreciated about the United States
Chapter 42 56 sec
The kindest thing anyone has ever done for him
Chapter 43 2 mins
A big lesson he’s earned in a deeper way that he wishes he could share with others
Like
Clip
Share
Transcript
More
Play Full
mute button
Madhavan Ramanujam - How to Price Products - [Invest Like the Best, EP.298]
My guest today is Madhavan Ramanujam. Madhavan quite... more
Oct 11 2022 56m
Innovation in Silicon Valley
Chapter 1 2 mins
[First question] How he arrived at a radically different way of building products
Chapter 2 3 mins
An example of coming up with a price before the product
Chapter 3 1 min
Distinctions between a willingness to pay and positive feedback
Chapter 4 3 mins
How to make sure you’re talking to the right potential customer in the first place
Chapter 5 2 mins
Productizing for different customer segments
Chapter 6 5 mins
Questions companies should be asking to get accurate feedback
Chapter 7 1 min
What he’s learned about the motivations of potential buyers
Chapter 8 1 min
What leaders, killers, and fillers are
Chapter 9 57 sec
Some of the biggest mistakes companies make while following his formula
Chapter 10 1 min
A rule of thumb for what is a benefit versus a feature
Chapter 11 3 mins
Five distinct pricing models for charging a customer
Chapter 12 2 mins
Whether or not the value piece of all of this revolves around time and money
Chapter 13 1 min
What he tells entrepreneurs about pricing their products that most surprises them
Chapter 14 4 mins
Defining the first four categories of failure
Chapter 15 1 min
Reasons why so many innovations fail to monetize and pricing being a CEO topic
Chapter 16 5 mins
Good rules that leaders can use to have a general sense for effective pricing
Chapter 17 2 mins
Behavioral changes and observations as the absolute price move up and down
Chapter 18 2 mins
Is there a pricing genius we should take note of?
Chapter 19 27 sec
The single question every leader should ask themselves
Chapter 20 2 mins
The kindest thing anyone has ever done for him
Like
Clip
Share
Transcript
More
Play Full
mute button
Scott Wilson - Non-Traditional Endowment Investing - [Invest Like the Best, EP.297]
My guest today is Scott Wilson. Scott is the CIO of ... more
Oct 4 2022 56m
Quantitative World vs. Private Equity
Chapter 1 2 mins
[First question] What he learned about markets from quant fixed income trading
Chapter 2 32 sec
How his experience shaped his degree of skepticism of the world
Chapter 3 1 min
The story that brought him to Grinnell College
Chapter 4 1 min
What his education was like back in 2010 and what seemed sensible and insane when he arrived
Chapter 5 1 min
The style of investment he learned at Grinnell compared to his style now
Chapter 6 1 min
His philosophy around trying to have more direct ownership
Chapter 7 1 min
Why their co-investment approach is outperforming the rest
Chapter 8 1 min
Lessons learned about choosing good partners and doing it effectively over time
Chapter 9 33 sec
Things that are most enjoyable about getting to know new managers
Chapter 10 1 min
The role that global travel and having boots on the ground plays in his success
Chapter 11 2 mins
Why they spend so much time in frontier and emerging markets
Chapter 12 1 min
Lessons learned from investing in China and thoughts on it today
Chapter 13 51 sec
What else he’s learned in continental Asia outside of China
Chapter 14 2 mins
Interests and red flags when it comes to investing in the venture space
Chapter 15 1 min
The worst things he sees from venture investors
Chapter 16 1 min
Whether or not venture investors should care more
Chapter 17 1 min
The virtues and vices in private equity and his thoughts on that space
Chapter 18 1 min
What percentage of investors in private equity are investors versus just involved to try and engineer returns
Chapter 19 2 mins
His impressions on hedge funds and the evolution of the hedge fund model
Chapter 20 1 min
The role that credit can play in a portfolio like the one he manages now
Chapter 21 1 min
Common characteristics of managers that perform well in credit
Chapter 22 2 mins
How he thinks about the sources of returns in the “other” portfolio category
Chapter 23 3 mins
Everything he’s learned about asset managers acting as asset gatherers
Chapter 24 2 mins
Ways he fights convergence and tracking error overseeing so much capital
Chapter 25 2 mins
What it’s like to go through the bad side of tracking error
Chapter 26 1 min
Thoughts on how the macro environment influences allocating time and resources
Chapter 27 1 min
What he sees as a normal level of tracking error for endowments and foundations
Chapter 28 1 min
Why such big pools of institutional capital tend to look so similar
Chapter 29 56 sec
Whether or not real estate sits somewhere between stocks and bonds
Chapter 30 2 mins
The cultivation of a talented investment team and effectively teaching investing
Chapter 31 1 min
Colliding managers in a fun and spirited way at meetings
Chapter 32 33 sec
An investing trip from his career that he finds most memorable
Chapter 33 43 sec
The kindest thing anyone has ever done for him
Chapter 34 2 mins
Whether or not the factors that sort winners from losers will be different today compared to a decade ago
Like
Clip
Share
Transcript
More
Play Full
mute button
Julio Vasconcellos & Mate Pencz - Investing in Latin America - [Invest Like the Best, EP.296]
My guests today are Julio Vasconcellos and Mate Penc... more
Sep 27 2022 1h 1m
Technology in America
Chapter 1 2 mins
[First question] A broad perspective on what is interesting in Latin American investing today Latin America Digital Report 2022
Chapter 2 55 sec
What makes up the existing 1.5% tech penetration index in Lat Am
Chapter 3 2 mins
Florian Hagenbuch, Mate Pencz Everything Will be Bought Online (Loft) ; David Velez Building the Branchless Network (Nubank) ; How important it is to parse by country when it comes to building businesses in LatAm
Chapter 4 3 mins
Overview of LatAm as a microcosm of fintech innovation happening really fast and what is most exciting in that sphere
Chapter 5 1 min
Why the adoption of PIX was so successful and how it maps onto the banking system
Chapter 6 4 mins
What PIX’s widespread adoption will enable for the coming wave of entrepreneurs
Chapter 7 3 mins
Demographics, GDP, growth rates, and inequality in LatAm
Chapter 8 2 mins
Shifting to remote work and how it’ll affect LatAm workers and talent
Chapter 9 4 mins
Macro tailwinds that matter when it comes to returns in these markes
Chapter 10 2 mins
What it feels like for an entrepreneur today compared to when Loft launched
Chapter 11 4 mins
Deeper themes and what needs to be unlocked for LatAm’s tech sector to look more like the US or China with big tech giants
Chapter 12 3 mins
The opportunity set in developing a software that serves small and medium businesses in LatAm
Chapter 13 2 mins
Sources of available funding for venture and private equity
Chapter 14 2 mins
What valuations look like and whether or not there’s an entry multiple discount
Chapter 15 2 mins
Seeking evidence that crypto is used in more valuable ways in emerging markets
Chapter 16 2 mins
Areas where LatAm is operating in a future state more so than elsewhere
Chapter 17 2 mins
What the right amount of global firm participation in capital partnerships looks like
Chapter 18 3 mins
Big standout lessons from their operating days
Chapter 19 2 mins
What is most exciting and concerning about their investing style and investing writ large in LatAm
Chapter 20 2 mins
The kindest thing anyone has ever done for Julio
Like
Clip
Share
Transcript
More
Play Full
mute button
Trina Spear - Billion Dollar Scrubs - [Invest Like the Best, EP.295]
My guest today is Trina Spear, a former investor at ... more
Sep 20 2022 49m
Building a Direct to Consumer Audience Online
Chapter 1 1 min
[First question] The original insight that lead to founding FIGS
Chapter 2 1 min
Why obvious opportunities can go so long before being seized
Chapter 3 2 mins
Key dimensions needed to improve the product and the early days
Chapter 4 1 min
Basic overview of a clothing retailer’s financial profile
Chapter 5 2 mins
Financing the business and the early stage cash flow cycle
Chapter 6 1 min
Strategies to manage workflow and making sacrifices
Chapter 7 2 mins
Advice for people trying to build their brands in a hands-on way
Chapter 8 1 min
The biggest calculated risk she took in the first five years
Chapter 9 2 mins
Building a foundation that allowed for such explosive growth
Chapter 10 2 mins
The story that allowed FIGS to connect with their customers
Chapter 11 1 min
Painting a picture of the size and scope of healthcare apparel
Chapter 12 2 mins
Things lazy companies do and thoughts on product variety
Chapter 13 1 min
Defining SKU productivity and what to do with low productivity products
Chapter 14 1 min
Chip Wilson Book ; Lessons learned from reading Chip’s story
Chapter 15 2 mins
Balancing a healthy relationship with your CFO
Chapter 16 1 min
Where she sees the most runway to tackle and continue to execute
Chapter 17 2 mins
A women-lead industry and her time spent with Meg Whitman
Chapter 18 1 min
The most essential jobs she feels she has and shouldn’t do as the CEO
Chapter 19 2 mins
Thoughts about relationships with investors and messaging
Chapter 20 1 min
What she’d be most focus on in founders if she was just an investor
Chapter 21 43 sec
The most stressful thing that has ever come across her desk
Chapter 22 45 sec
What types of things bring her the most joy in building FIGS
Chapter 23 1 min
Philosophy of hiring given their small team and when it’s okay to hire
Chapter 24 51 sec
Whether or not there’s a role for non A players in businesses
Chapter 25 1 min
The kindest thing anyone has ever done for her
Like
Clip
Share
Transcript
More
Play Full
mute button
Gabriel Leydon - How Web3 Onboards a Billion Users - [Web3 Breakdowns, EP.37]
Today, we are sharing an episode of Web3 Breakdowns ... more
Sep 15 2022 59m
NFTs
Chapter 1 9 mins
[First question] What free-to-own gaming means and why it’s exciting
Chapter 2 51 sec
Pre-existing behavior that sets up free-to-own for success
Chapter 3 1 min
The progression from PFP NFTs to clubs and the road ahead
Chapter 4 3 mins
Overview of the business and monetization model for free-to-own games
Chapter 5 4 mins
The story of DigiDaigaku, their mechanics, the drops, and what lead to their creation
Chapter 6 2 mins
Balancing supply and demand in a free-to-own market
Chapter 7 1 min
Creativity and extensions of the DigiDaigaku NFTs
Chapter 8 1 min
Tiering, breeding and the role the Genesis series will play in the Digi universe
Chapter 9 2 mins
The level of brand marketing NFTs will unlock for businesses
Chapter 10 1 min
How free-to-own will be the primary monetization method for brands
Chapter 11 1 min
A future with a global marketing shift towards digital property and economies
Chapter 12 2 mins
Why most of the winning PFP projects are of unique characters
Chapter 13 6 mins
His Twitter strategy and how he’s created such a fervor around him
Chapter 14 25 sec
What will define the legendary marketers over the coming decade
Chapter 15 1 min
Interoperability needed to make real-world NFT uses appealing to consumers
Chapter 16 55 sec
Whether or not we’ll see more token-gated business in the future
Chapter 17 3 mins
Stable Diffusion and his impression of the new AI art generating bots
Chapter 18 1 min
What great distribution looks like in a digitally native world
Chapter 19 3 mins
The emphasis of innovation taking place in the metaverse being a bad thing
Chapter 20 1 min
Things he most admires in adjacent games and creators in his world
Chapter 21 1 min
Unique game mechanics that Web3 technology unlocks
Chapter 22 3 mins
NFTs will be the gateway for people to acquire crypto
Like
Clip
Share
Transcript
More
Play Full
mute button
Harley Finkelstein - Building the Entrepreneurship Company - [Invest Like the Best, EP.294]
My guest today is Harley Finkelstein. Harley is the ... more
Sep 13 2022 1h 5m
Communicating with Wall Street
Chapter 1 3 mins
[First question] His interpretation and definition of a person’s life's work
Chapter 2 2 mins
The story of the riverstone and the average polished executive
Chapter 3 4 mins
The thing he can’t help but do; and focusing on our compulsions
Chapter 4 3 mins
How he would boil things down to the most simple entrepreneurial formula; Distilled
Chapter 5 4 mins
What is harder and easier about new business formation today
Chapter 6 3 mins
The countervailing forces for small-to-medium business entrepreneurship
Chapter 7 4 mins
What he’s learned about operationalizing ideas and mentor lessons
Chapter 8 1 min
A piece of fortune cookie advice that he finds terrible
Chapter 9 4 mins
How Brands Grow ; his philosophy on marketing & distribution
Chapter 10 3 mins
The most effective distribution strategies he’s seen work in Shopify that might be portable to other businesses
Chapter 11 2 mins
What it was like getting their first app developer for the Shopify app store
Chapter 12 4 mins
The state of ecommerce today writ large and what trends are interesting
Chapter 13 3 mins
Lessons learned about the digital places that people are buying
Chapter 14 3 mins
What it’s been like as an executive working at a company that had their stock price explode over the pandemic
Chapter 15 1 min
Tips for communicating effectively with Wall Street
Chapter 16 55 sec
An investor that stands out in memory that really impressed him
Chapter 17 1 min
Important aspects of his world that are worth mentioning
Chapter 18 2 mins
Lessons learned about motivating people through DJing
Chapter 19 4 mins
Whether or not reading the crowd can apply to business
Chapter 20 1 min
The kindest thing anyone has ever done for him
Like
Clip
Share
Transcript
More
Play Full
mute button
Mitch Lasky - The Business of Gaming - [Invest Like the Best, EP.293]
My guest today is Mitch Lasky. Mitch is a partner at... more
Sep 6 2022 1h 13m
Phil Spencer's Business Moves
Chapter 1 2 mins
[First question] Why there aren’t more famous gaming investors
Chapter 2 2 mins
The most important features of the modern gaming business model
Chapter 3 51 sec
Developing his aesthetic taste and investing decision skill
Chapter 4 1 min
What makes a game fun
Chapter 5 1 min
How delivering a pleasurable active user experience differs from passive content and media
Chapter 6 1 min
The developers of Doom being the first real modern video game company
Chapter 7 1 min
Half-Life’s important role in the development of the gaming industry
Chapter 8 3 mins
The powerful notion of the platform-based publisher model
Chapter 9 2 mins
How some of the big game aggregators get started in the first place
Chapter 10 1 min
What Riot can teach non-gaming businesses about business writ large
Chapter 11 4 mins
Ways that the change from physical games to downloads changed monetization
Chapter 12 3 mins
How to quantify an economic model in the new paradigm of superfan monetization
Chapter 13 3 mins
What the shift in gaming platforms has done to the business model
Chapter 14 2 mins
The impact of Apple’s privacy changes on gaming revenue
Chapter 15 2 mins
How the access to professional game engines and a lower friction environment will change the industry
Chapter 16 2 mins
Whether or not there is a step beyond mobile
Chapter 17 2 mins
Ways platforms like Twitch and Discord have influenced gaming
Chapter 18 2 mins
What he’s learned about games that allow them to seemingly exist forever
Chapter 19 1 min
Signs of a healthy gaming community
Chapter 20 1 min
The role of celebrities and influencers and generating retained audiences
Chapter 21 5 mins
Whether or not crypto will unlock new opportunities for in-game monetization
Chapter 22 1 min
Key categories of motivators that could replace a ponzi-style in-game inflation
Chapter 23 3 mins
Contrasting League of Legends versus a Ready Player One style world
Chapter 24 2 mins
Emerging technologies and trends that may revolutionize the industry
Chapter 25 2 mins
A future with further consolidation on distribution and power
Chapter 26 2 mins
The most genius game pattern he’s ever played
Chapter 27 2 mins
What attributes will define the great game investors in the coming decades
Chapter 28 4 mins
How much his experience lends itself to investing in other sectors
Chapter 29 2 mins
The kindest thing anyone has ever done for him
Like
Clip
Share
Transcript
More
Play Full
mute button
David Senra - Passion & Pain - [Invest Like the Best, EP.292]
My guest today is David Senra. David has studied his... more
Aug 30 2022 1h 22m
Relentless Execution.
Chapter 1 3 mins
[First question] When he first fell in love with reading
Chapter 2 3 mins
What’s rooted in his own history that’s made him obsessive about studying history’s great entrepreneurs and founders Founders Podcast
Chapter 3 3 mins
The first time he connected with someone as a positive role model that he was reading about
Chapter 4 4 mins
How often obsession is apparent in the founders he’s studied across hundreds of biographies
Chapter 5 4 mins
What is often behind obsession and how people listening can apply the lessons to their own lives
Chapter 6 4 mins
The dynamic and relationship between inspiration and perspiration
Chapter 7 4 mins
Commonalities between the layers of leadership and support underneath founders
Chapter 8 6 mins
Where else he’s seen ego rear its head in good and bad ways
Chapter 9 2 mins
How often do great founders break the law or enter gray areas of it
Chapter 10 3 mins
The role constant learning and listening plays in success
Chapter 11 7 mins
Talking about how anything worth doing is worth doing to excess
Chapter 12 6 mins
Describing the soul of founders and businesses
Chapter 13 5 mins
What he’s learned about all of these founders as it relates to marketing
Chapter 14 3 mins
A common story that process is often art
Chapter 15 6 mins
Who his idols are in podcasting specifically
Chapter 16 4 mins
Major aspects of people he’s studied that haven’t been discussed yet
Chapter 17 3 mins
The kindest thing anyone has ever done for him
Like
Clip
Share
Transcript
More
Play Full
mute button
Robert Smith - Investing in Enterprise Software - [Invest Like the Best, EP.291]
My guest today is Robert Smith, the founder, Chairma... more
Aug 23 2022 56m
Vista's Biggest Mistakes
Chapter 1 3 mins
[First question] What the enterprise software market looks and feels like to him
Chapter 2 3 mins
Whether or not software is becoming a saturated market and what will drive demand over the coming decades
Chapter 3 2 mins
Bringing an engineering mindset to enterprise software investing and culture
Chapter 4 1 min
A single change he made to a business that stands out most in memory
Chapter 5 3 mins
Qualities that are most critical in defining a good enterprise software company
Chapter 6 2 mins
How the profile of companies he’s bought has changed over the years
Chapter 7 3 mins
Categories of software he tends to gravitate towards
Chapter 8 3 mins
Evolving his model for considering what multiple to pay for a business and thinking about p/e growth multiples
Chapter 9 2 mins
Lessons learned about customer churn over his twenty two year career
Chapter 10 2 mins
Capital cycles and how much they truly impact the software world
Chapter 11 2 mins
What elements of building Vista have most appealed to him over the years
Chapter 12 3 mins
Changing their investment strategy as the world continues to change
Chapter 13 1 min
The war for talent and what his senior team would debate most
Chapter 14 1 min
Biggest mistakes Vista has made and what they taught him
Chapter 15 2 mins
What has him most insecure or paranoid about the platform he’s built
Chapter 16 1 min
The advice he’d give on having good relationships with LPs
Chapter 17 1 min
The largest risk he or Vista has ever intentionally taken
Chapter 18 3 mins
What he’s learned about having a winning negotiations and sales approach
Chapter 19 38 sec
Who he’d give all of his capital to outside of Vista
Chapter 20 3 mins
How he arrived at the themes he tends to be philanthropic towards
Chapter 21 1 min
The work he does in the foster world
Chapter 22 1 min
The kindest thing anyone has ever done for him
Like
Clip
Share
Transcript
More
Play Full