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Invest Like the Best with Patrick O'Shaughnessy

Exploring the ideas, methods, and stories of people that will help you better invest your time and money. Learn more and stay-up-to-date at https://joincolossus.com/
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Invest Like the Best with Patrick O'Shaughnessy
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Now displaying: December, 2021
Dec 28, 2021

My guest today is Orlando Bravo, co-founder and Managing Partner of leading private equity firm, Thoma Bravo. Thoma Bravo manages over $90bn of assets and is best known for investing in software and technology businesses. It was Orlando who led the firm’s early entry into software buyouts some twenty years ago, and he has overseen more than 350 software acquisitions since. There are few, if any, people better placed to discuss private equity and software investing. Please enjoy this excellent discussion with Orlando Bravo.

 

For the full show notes, transcript, and links to the best content to learn more, check out the episode page here.

 

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This episode is brought to you by Tegus. Tegus has built the most extensive primary information platform available for investors. With Tegus, you can learn everything you’d want to know about a company in an on-demand digital platform. Investors share their expert calls, allowing others to instantly access more than 20,000 calls on Affirm, Teladoc, Roblox, or almost any company of interest. All you have to do is log in. Visit tegus.co/patrick to learn more.

 

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Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes

 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

 

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

 

Follow us on Twitter: @patrick_oshag | @JoinColossus

 

Show Notes

[00:02:36] - [First question] - His belief about an opportunity/capital mismatch in private equity

[00:04:26] - Adjusting his own approach to take advantage of seemingly niche opportunities

[00:06:13] - Differences between software businesses they invest in versus traditional ones

[00:08:25] - Outline of how he runs their four-hour portfolio meetings

[00:09:53] - Overview of the very first deal he ever made in the software sector

[00:14:01] - The dissonance between the average SaaS company and the ones they try to manage

[00:18:22] - Major contributors that allow for their higher margins

[00:20:16] - Common mistakes of companies that mis-invest capital for growth only

[00:22:28] - Defining what market leader means writ large

[00:23:45] - Why the subsector of cyber security is such a good opportunity set

[00:26:25] - The evolving nature of the private equity world in general

[00:28:41] - Where returns will come from going forward

[00:31:47] - How good the opportunity for returns in this style of investing today is

[00:35:32] - Lessons learned on knowing when to exit or sell a position

[00:37:59] - How short their holding periods can be and how much influence they can have in such a short time

[00:40:04] - Surprising things about deal-making that he’s learned over his career

[00:41:20] - Difficulties and points of frictions in deals that still exist for him today

[00:43:11] - What part of the deal-making process he loves the most

[00:44:30] - If your job title has a C in it you’re not allowed to complain about it

[00:46:27] - Deeply held beliefs about operating excellence

[00:47:33] - What the word service means to him given everything we’ve talked about 

[00:50:27] - How we do a better job of inviting talent into this space

[00:52:51] - How decentralization will define the 2020s and beyond

[00:55:48] - What is most interesting about Web3 that might affect cyber security

[00:57:42] - Where there is a lack in innovation in private equity today

[01:00:45] - Advice for young talent for building their careers

[01:03:16] - The kindest thing that anyone has ever done for him

Dec 23, 2021

My guest today is Nick Saltarelli, co-founder of the functional chocolate bar business, Mid-Day Squares. Nick started the company with his wife and brother-in-law a few years ago to build on a simple idea: if the big chocolate bar brands were to start today, what would they look like?

 

In our conversation, we discuss the importance of Mid-Day Squares’ $100 million revenue target, what’s wrong with the CPG industry today, and how to keep a long-term mindset while making the most of every day. Please enjoy this unique conversation with Nick Saltarelli.

 

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

 

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This episode is brought to you by Pilot. Pilot handles your startup’s finance, accounting, and tax prep needs, so you can focus on what matters most—building your business. Join over 1,000 startups that rely on Pilot to help them scale. Founder’s Field Guide listeners get 20% off their first six months. Get in touch with Pilot at https://pilot.com/founders

 

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Founder's Field Guide is a property of Colossus, LLC. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes.

 

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

 

Follow us on Twitter: @patrick_oshag | @JoinColossus

 

Show Notes

[00:02:01] - [First question] - What Mid-Day Squares is and how he started the business

[00:04:48] - Why they’re so publicly open about their company’s goals

[00:09:05] - Major lessons he learned from his father’s early passing and being around very successful entrepreneurs at a young age 

[00:16:51] - What long term thinking unlocks for him in short term progress

[00:21:05] - Becoming unexpectedly close and learning from Rory Olson 

[00:25:44] - What Rory taught him about deal-making

[00:28:35] - Lessons from Rory about raising capital

[00:33:25] - Opportunities in a seemingly oversaturated market like chocolate

[00:42:46] - An example of doing something contrarian that worked out

[00:47:11] - Their unique approach to marketing Mid-Day Squares

[00:57:33] - Lessons learned about building a manufacturing operation after years in China

[01:02:35] - What we can expect from Mid-Day Squares in the near future

[01:06:59] - The kindest thing anyone has ever done for him

[01:08:05] - Mid-Day Squares Uncensored Podcast

Dec 21, 2021

My guest today is Jenny Johnson, President and CEO of one of the world’s largest asset managers, Franklin Templeton. Jenny joined the business in 1988 and has worked in the organization ever since. In early 2020 she became CEO of Franklin, which now manages some $1.5 trillion. I should, of course, note that I met Jenny as our two firms explored a partnership, which we cemented 3 months ago when we announced that Franklin Templeton would be acquiring O'Shaughnessy Asset Management.

 

During our conversation, we discuss Jenny’s thoughts on leadership, how she manages the needle-moving problem that afflicts many large companies, and the ways in which she sees private markets becoming more accessible to retail investors in the future. Please enjoy this great conversation with Jenny Johnson.

 

For the full show notes, transcript, and links to the best content to learn more, check out the episode page here.

 

-----

 

This episode is brought to you by Tegus. Tegus has built the most extensive primary information platform available for investors.

 

With Tegus, you can learn everything you’d want to know about a company in an on-demand digital platform. Investors share their expert calls, allowing others to instantly access more than 20,000 calls on Affirm, Teladoc, Roblox, or almost any company of interest. All you have to do is log in. Visit tegus.co/patrick to learn more.



-----

 

At WatchBox, the world’s finest watches are at your fingertips with an ever-expanding collection of luxury timepieces, all certified authentic and collector quality. WatchBox’s global team of expert client advisors is ready to help you find the watch you’ve always wanted. Step into the collector’s circle at thewatchbox.com/patrick

 

-----



Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes

 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

 

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

 

Follow us on Twitter: @patrick_oshag | @JoinColossus

 

Show Notes

[00:03:19] - [First question] - The four P’s of leadership and what she thinks are the most important roles of a CEO 

[00:06:00] - The difficulty of finding and recruiting great people and keeping them invested 

[00:07:18] - Things she looks for in her senior leadership team

[00:07:59] - Knowing when to be more or less involved as a leader

[00:09:30] - Her takeaways from working in a family-owned business

[00:11:20] - Advice she’d give to families who are building businesses together

[00:12:06] - Thoughts on the role technology will play in the asset management industry

[00:16:13] - Costs and frictions that blockchains could alleviate

[00:18:17] - General views on disruption and considering ones position when thinking about the future

[00:20:09] - Knowing when to start a project internally or acquire an existing project

[00:23:10] - The hardest things about effective M&A decisions

[00:23:42] - Overseeing a hybrid model of singular focus between multiple investment groups

[00:28:26] - The pros and cons of active management against passive adoption

[00:31:15] - Costs and fees in the industry and how they might change in the future 

[00:33:04] - Talking to clients when they don’t have one specific view on strategy

[00:34:57] - When consensus is helpful and appropriate for making important decisions

[00:36:10] - Formative experiences in her career that has shaped her worldview

[00:38:34] - Managing emotions through seemingly chaotic situations

[00:39:13] - The impacts on psychology when being a top performer and an average one

[00:41:15] - Managing and adapting strategy when faced with highs and lows 

[00:42:55] - Acquiring alternative managers and defining what alternative assets are

[00:46:26] - Relevant trends on how capital is pooled and their client base over time

[00:47:52] - What is under-discussed in the world of asset management today writ large

[00:49:01] - Other leaders she’s met or knows that have had her in awe

[00:50:30] - What about Cathie Wood has made her story and approach so successful

[00:51:38] - How she runs a great board meeting and ways to improve meetings themselves 

[00:53:34] - Lessons learned about time management as the leader of a public company

[00:54:52] - What purpose means to her 

[00:56:18] - Ways we can incentivize young and new people to start investing

[00:59:10] - Her favorite things that her dad has taught her and how she’d describe him 

[01:00:57] - What has her most excited about the future  

[01:01:34] - The kindest thing that anyone has ever done for her

Dec 14, 2021

My guest today is Doug Colkitt. Doug has spent his career searching for and trading inefficient markets, first at Citadel’s high-frequency trading group, then for himself, and then as an operator building CrocSwap - a decentralized exchange or DEX designed to bring modern functionality to crypto markets, which is closer to what large traders have come to expect from a modern electronic market like the NASDAQ. 

 

My interest in market infrastructure has continued to grow since my great conversation with FTX founder Sam Bankman-Fried. So my conversation with Doug covers the evolution of market and trading infrastructure. We unpack the trading stack as it exists today, dive into DeFi’s innovations, and explore the new category of single contract DEXs that Doug is creating. After learning so much from Doug about how markets function and how crypto markets should function, I became an investor in his new business via my venture capital firm Positive Sum. Please enjoy this great conversation with Doug Colkitt.

 

For the full show notes, transcript, and links to the best content to learn more, check out the episode page here.

 

-----

 

This episode is brought to you by Tegus. Tegus has built the most extensive primary information platform available for investors.

 

With Tegus, you can learn everything you’d want to know about a company in an on-demand digital platform. Investors share their expert calls, allowing others to instantly access more than 20,000 calls on Affirm, Teladoc, Roblox, or almost any company of interest. All you have to do is log in. Visit tegus.co/patrick to learn more.



-----

 

At WatchBox, the world’s finest watches are at your fingertips with an ever-expanding collection of luxury timepieces, all certified authentic and collector quality. WatchBox’s global team of expert client advisors is ready to help you find the watch you’ve always wanted. Step into the collector’s circle at thewatchbox.com/patrick

 

-----



Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes

 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

 

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

 

Follow us on Twitter: @patrick_oshag | @JoinColossus

 

Show Notes

[00:03:31] - [First question] - Doug’s career and history working with markets

[00:08:55] - Defining what a trading stack is 

[00:13:41] - How HFT firms are such reliable money-making models

[00:16:27] - What’s at the cutting edge of traditional markets that provides an edge

[00:18:45] - The mechanical parts of infrastructure involved in building an exchange

[00:21:00] - Classes of data that matter for operating an exchange

[00:22:11] - Capacity and what good returns are as an HFT firm

[00:28:45] - Overview of the mechanics of an AMM

[00:31:53] - Earning a yield as a liquidity provider

[00:33:59] - Other ways to think about AMMs and liquidity providers

[00:36:42] - Key players in the AMM space and the evolution of them

[00:41:20] - How asset holders can approach DEX tools and be liquidity providers

[00:42:55] - The function of an exchange’s native token

[00:45:25] - Token distribution and how to earn them without buying them

[00:48:31] - How you receive payment for providing liquidity

[00:51:31] - What CrocSwap will do and what a single contract DEX unlocks

[00:57:36] - How CrocSwap is able to do this when other exchanges can’t

[00:59:27] - What single contracts will improve for users 

[01:00:43] - The impact CrocSwap will have for all participants writ large

[01:02:28] - Whether or not CrocSwap will cultivate an ecosystem

[01:03:30] - What’s next for CrocSwap in the near future

[01:04:58] - The promise of DeFi and the future of blockchain technology

[01:07:04] - Whether or not DeFi is a threat to centralized exchanges

[01:09:52] - Defining what MEV is and why it’s important for DeFi

[01:13:04] - Missing pieces in the DeFi world and how we can address them

[01:15:24] - The kindest thing anyone has ever done for him

Dec 7, 2021

My guests today are Philip Rosedale and Bill Gurley. Philip created Second Life in the early 2000s and helped build it into the largest virtual 3D world ever created at the time. Frequent listeners will recognize Bill, who was an investor in Second Life via Benchmark Capital. During the conversation, we cover the fascinating story of Second Life and the billion-dollar economy that persists through to this day. Bill and Phillip share their key learnings from the experience, including the importance of usability, their views of the current metaverse opportunity, and what excites them most about the current focus on virtual realities. If you’re curious about what the metaverse might become, these two experts have seen much of this already and are kind to share their lessons with us. Please enjoy my conversation with Phillip and Bill.

 

For the full show notes, transcript, and links to the best content to learn more, check out the episode page here.

 

-----

 

This episode is brought to you by Tegus. Tegus has built the most extensive primary information platform available for investors.

 

With Tegus, you can learn everything you’d want to know about a company in an on-demand digital platform. Investors share their expert calls, allowing others to instantly access more than 20,000 calls on Affirm, Teladoc, Roblox, or almost any company of interest. All you have to do is log in. Visit tegus.co/patrick to learn more.

 

-----

 

At WatchBox, the world’s finest watches are at your fingertips with an ever-expanding collection of luxury timepieces, all certified authentic and collector quality. WatchBox’s global team of expert client advisors is ready to help you find the watch you’ve always wanted. Step into the collector’s circle at thewatchbox.com/patrick

 

-----



Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes

 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

 

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

 

Follow us on Twitter: @patrick_oshag | @JoinColossus

 

Show Notes

[00:03:22] - [First question] - The origin story of Second Life and why they created it

[00:05:38] - How many people were playing Second Life at its peak, the in-game economy and its growth trajectory

[00:06:49] - The interface between the in-game currency and its function for players

[00:10:53] - An example of early entrepreneurship and user-created IP in Second Life

[00:12:13] - Was technology a rate limiter to success in such an early version of the metaverse?

[00:14:35] - What was most exciting about creating it and it’s early-stage potential

[00:18:23] - Why Unity isn’t more adopted by creators and players like Minecraft

[00:24:42] - Defining what the metaverse means to each of them today 

[00:28:50] - What Discord has taught them about aggregating people digitally

[00:33:02] - Simultaneously crossing the digital chasm and the uncanny valley 

[00:38:16] - Key differences between games and platforms and the role of purpose

[00:42:04] - Why cryptocurrencies and blockchains haven’t produced experiences akin to the virtual Travis Scott concert

[00:47:13] - Why removing friction and centralizing financial structures can help growth and thoughts on play to earn gaming and user spending

[00:53:27] - Digital asset ownership and digital trustless exchanges in the metaverse

[00:57:30] - Pros and cons of today’s speculative digital asset valuations

[01:01:05] - Interesting pockets of opportunity that could benefit the metaverse ecosystem

[01:04:28] - How they’d build and construct an ETF with metaverse exposure

[01:07:18] - Thoughts on AR and VR and which holds more promise for public adoption 

[01:08:02] - Surprising findings about the role audio plays in digital worlds  

[01:10:23] - What they’re watching most closely in this emergent sector

[01:11:29] - Limitations of visual and sonic barriers when recreating real-world interactions 

[01:12:42] - The kindest things anyone has ever done for them 

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