169 episodes

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 InvestorFieldGuide.com

Invest Like the Best Patrick O'Shaughnessy

    • Investing

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 InvestorFieldGuide.com

    [REPLAY] What You Learn About Business Deals After: 12,000 Deals Reviewed, 1,500 Deep Dives, 125 Site Visits, and 7 Portfolio Companies with Brent Beshore - [Invest Like the Best, EP.100]

    [REPLAY] What You Learn About Business Deals After: 12,000 Deals Reviewed, 1,500 Deep Dives, 125 Site Visits, and 7 Portfolio Companies with Brent Beshore - [Invest Like the Best, EP.100]

    For the 100th episode, I’ve brought back my good friend Brent Beshore. Brent was the 10th guest on the podcast, after we met because of a mutual interest in capital allocation. I quickly learned that Brent was one of the most unique and thoughtful investors around. He was an entrepreneur from the moment he left school, trying many different things before finding a fit buying smaller business with the intention of owning them forever.

    What amazes me about Brent is his encyclopedic understanding of business and the nuances of different business models and deal structures. This comes from reps. He and his team have looked at about 12,000 deals over the years, at every kind of business that you could imagine. I’ve been with him when he goes through this process and it’s fun to hear what makes certain businesses stand out from others, which is largely the topic of this conversation.

    You all know transparency is key for me, so it’s important to know that my family and I are investors in a fund called permanent equity, run by Brent and his firm Adventure.es.

    To commemorate this milestone episode, I can think of no one better than Brent, because he exemplifies what has made this podcast so fun for me: learning from other people who are willing to share what they themselves have learned through fun, blood, sweat, and tears. Please enjoy our conversation, and thank you so much for coming along on this journey. I can’t tell you how much it means to me.
    For more episodes go to InvestorFieldGuide.com/podcast.
    Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub.
    Follow Patrick on Twitter at @patrick_oshag
    Show Notes
    2:02 - (First Question) – How does he think about optimizing risk in terms of the capital stack when looking at deals
    5:27 – What conditions would they add debt down the road after investing in a company
    6:52 – What business sectors are most intriguing for Morgan to invest in right now
                6:57 – Trent Griffin Podcast
    9:34 – Why no HVAC businesses if it’s such an attractive sector
    13:56 – thoughts on rolling up similar businesses and horizontal scale
    16:04 – Another industry Brent would focus on
    18:02 – Difference between property management in larger cities vs smaller metro areas
    18:51 – What role does profit margin play when Brent is evaluating a business
    22:46 – The appeal of a hyper cyclical business
                22:52 – Brent Beshore Podcast Episode
    27:27 – Favorite counter cyclical business
    28:14 – How they judge assets, tangible vs intangible assets
    33:58 – How does he think about wage inflation when considering the cost of a business
    37:21 – His fascination with pet crematoriums
    38:57 – History of the permanent equity fund and the changes by having a larger pool of capital
    43:48 – Pitching investors on a new structure for the business
    46:14 – How will this business model scale
    Learn More
    For more episodes go to InvestorFieldGuide.com/podcast. 
    Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub
    Follow Patrick on twitter at @patrick_oshag

    • 51 min
    Chetan Puttagunta – Go Slow to Go Fast: Software Building and Investing - [Invest Like the Best, EP.156]

    Chetan Puttagunta – Go Slow to Go Fast: Software Building and Investing - [Invest Like the Best, EP.156]

    My guest this week is a good friend and a business mentor of mine. Chetan Puttagunta is a general partner at Benchmark Capital and has a remarkable track record of investing in early-stage software businesses, including several like Mulesoft, MongoDB, and Elastic that went on to be public companies.
    Chetan has been my key guide for understanding the world of enterprise software as we at O’Shaughnessy Asset Management have built an investing platform called Canvas. His advice has been critical to our early success. In this episode, we explore the history of software and software investing, and go into the details on how to build and grow new software businesses. We discuss product, sales and marketing, recruiting, scaling, and everything in between.
    Please enjoy this great conversation with one of my favorite business and investing thinkers.
    For more episodes go to InvestorFieldGuide.com/podcast.
    Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub.
    Follow Patrick on Twitter at @patrick_oshag
     
    Show Notes
    1:34 – (First Question) – How Chetan found MongoDB and decided to invest in it
    8:01 – The evolution of databases in the growth of technology
    16:19 – Market penetration of this space and what investors should be thinking about
    21:46 – Advice how companies can build software effectively
    25:12 – Tactics to effectively implement empathy led product building
    30:33 – Companies asking users what to build vs telling users what they want
    34:26 – The need for the right capital, and patient capital in particular
    37:55 – Creating the perfect customer experience
    44:37 – Common reasons they don’t invest in a company
    48:48 – Lessons on scaling, especially in sales and marketing
    52:47 – Best recruiting pipeline strategies
    59:56 – Pitfalls of unit economic traps
                1:00:23 – The Dangerous Seduction of the Lifetime Value (LTV) Formula
                1:01:34– The Hierarchy of Engagement
    1:02:18 – What has changed for Chetan in his time working with the team at Benchmark
    1:06:009 – Later stage life cycle business considerations and Amazon’s AWS
    1:13:29 – The business model of open-source software
    1:15:54 – Being default open
    1:17:53 – Kindest thing anyone has done for Chetan
     
    Learn More
    For more episodes go to InvestorFieldGuide.com/podcast. 
    Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub
    Follow Patrick on Twitter at @patrick_oshag

    • 1 hr 20 min
    Rebecca Kaden – Thesis Driven Investing - [Invest Like the Best, EP.155]

    Rebecca Kaden – Thesis Driven Investing - [Invest Like the Best, EP.155]

    My guest today is Rebecca Kaden, a partner at famed venture firm union square ventures. USV is known for thesis-driven investing, which is the topic of our conversation. Rebecca walks us through the evolution of USV’s thesis into its third generation, and from there we explore many of the most interesting and exciting areas of business, technology, and learning. Please enjoy our conversation
    For more episodes go to InvestorFieldGuide.com/podcast.
    Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub.
    Follow Patrick on Twitter at @patrick_oshag
    Show Notes
    1:11 – (First Question) – An overview of Union Square Ventures Thesis 3.0
    7:49 – Core changes that can help any community
    9:59 – Ways to fix the broken education system
    13:41 – Gap between job preparedness and the education system
    14:44 – Companies creating education systems to prepare people for careers in their field
    18:49 – Most unique technological solution for people to educate themselves
    22:00 – Ways to improve access to capital
    26:49 – The distribution problem in capital markets
    28:19 – How does she assess an early-stage company and its team’s ability to assess their ability to maximize distribution
    30:56 – Digital marketing and why it could be broken
    34:22 – Examples of masterful marketing
    36:07 – How they are focused on improving wellbeing, their first focus on healthcare
    39:35 – Wellbeing on their focus on community
                41:29– The Art of Community: Seven Principles for Belonging
    45:30 – Her thoughts on mentorship
    48:23 – What she has learned in her time at USV
    51:50 – Kindest thing anyone has done for Rebecca
    Learn More
    For more episodes go to InvestorFieldGuide.com/podcast. 
    Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub
    Follow Patrick on Twitter at @patrick_oshag

    • 54 min
    Matt Clifford – Investing Pre-Company - [Invest Like the Best, EP.154]

    Matt Clifford – Investing Pre-Company - [Invest Like the Best, EP.154]

    My guest today is Matt Clifford. He’s the co-founder of Entrepreneur First, the world’s leading talent investor. They invest “pre-company” by helping the best people in cities around the world find a co-founder, develop an idea, and start a company. So far, they’ve helped 1000 people start 200 companies worth a combined $1.5B. This conversation covers their entire ecosystem and holds lessons for anyone building a business. I especially loved Matt’s ideas on the history of ambition.
     
    Please enjoy our conversation.
     
    For more episodes go to InvestorFieldGuide.com/podcast.
    Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub.
    Follow Patrick on Twitter at @patrick_oshag
     
    Show Notes
    1:20 – (First Question) – An overview on talent investing
    4:37 – The history of ambition
    10:08 – How do they search for ambitious people
    12:21 – What happens early on for these formed teams
    17:43 – Assigning an idea to a talented team
    20:52 – Opportunities in deep technology
    27:16 – A closer look at the hardware and machinery of the deep technology changes
    30:54 – The geographical focus of venture capital investments
    37:16 – Problems with the way early-stage investment world works
    41:22 – People who are creating value in a management company and how they manage their investments
    55:12 – Advice to people creating investment companies and pricing power
    1:00:31 – The power of cities
    1:02:46 – Topics they cover in their newsletter; technological sovereignty as one example
    1:04:11 – Experience and thoughts on China
                1:06:51 – A.I. Nationalism
    1:12:03 – Kindest thing anyone has done for Matt
     
    Learn More
    For more episodes go to InvestorFieldGuide.com/podcast. 
    Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub
    Follow Patrick on twitter at @patrick_oshag

    • 1 hr 14 min
    Peter Buffett – Finding Your Note - [Invest Like the Best, EP.153]

    Peter Buffett – Finding Your Note - [Invest Like the Best, EP.153]

    My guest today is Peter Buffett. Peter is a musician, composer, author, and philanthropist. Peter is an Emmy Award winner, New York Times best-selling author and co-chair of the NoVo Foundation. We discuss music, community, philanthropy, and finding one's note in life. This is a very different episode much more about life in general, with no business or investing discussed. Like his father Warren, Peter has the gene for phrasing ideas in memorable ways, and I think you’ll find many great phrases in this chat that will stick with you. I’ve been thinking about Peter's idea making sure those in your life are safe, seen, and celebrated ever since our chat.
    Please enjoy.
    For more episodes go to InvestorFieldGuide.com/podcast.
    Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub.
    Follow Patrick on Twitter at @patrick_oshag 
    Show Notes
    1:27 - (First Question) – Welcome and small talk
    1:35 – Why Peter is in Kingston and how it plays into his foundation work
    4:01 – How moving from the city to the country changed Peter
    6:27 – Seeing connections vs living abstractions
    7:30 – What is the Nova Foundation
    11:03 – Historical points that inform his views
    13:51 – Identifying qualitative negative side effects and which ones they are attacking
    17:51 – What makes for effective community 
    20:22 – Linkage between consumption and individualism
    23:55 – The cultivation of work ethic, curiosity, and education
                23:57 – Life Is What You Make It: Find Your Own Path to Fulfillment
    27:22 – Early exploration of his curiosity
    32:26 – What has music taught Peter about music that is unique to that experience
    34:26 – Most memorable question a person has asked Peter at his concert and conversation series
    36:46 – What makes for good relationships, in particular marriage
    42:03 – What keeps people from putting in the work into a relationship
    45:11 – What he has learned about being a good friend
    46:29 – How does one person have a relationship with a large community
    49:21 – Dark sides of the philanthropic world
                49:54 – The Charitable-Industrial Complex
    53:21 – Dignity: Seeking Respect in Back Row America
    55:55 – What one spot would he send everyone to learn
    57:48 – Traumas and helping people find their note
                57:49 – The Body Keeps the Score: Brain, Mind, and Body in the Healing of Trauma
                1:00:38 – How to Change Your Mind: What the New Science of Psychedelics Teaches Us About Consciousness, Dying, Addiction, Depression, and Transcendence
    1:02:24 – What is he most interested in right now: how to best use Nova’s funds
    1:04:45 – Lessons from family
    1:07:22 – Kindest thing anyone has done for Peter
    Learn More
    For more episodes go to InvestorFieldGuide.com/podcast. 
    Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub
    Follow Patrick on twitter at @patrick_oshag

    • 1 hr 9 min
    Ben Savage – All Things Fintech Investing - [Invest Like the Best, EP.152]

    Ben Savage – All Things Fintech Investing - [Invest Like the Best, EP.152]

    My guest today is Ben Savage, a partner at Clocktower ventures. Ben is focused on financial technology, fintech, investing which is the topic of our conversation.

    I’ve been making the fintech is rounds of late, and plan on making a few of these conversations public. Ben is the first in what may be a mini-series because of the sheer amount I learned in our discussion.

    We cover all aspects of the fintech ecosystem. I hope you enjoy.
    For more episodes go to InvestorFieldGuide.com/podcast.
    Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub.
    Follow Patrick on Twitter at @patrick_oshag
     Show Notes
    1:15 (First Question) – The market portfolio and how technology will move us away from liquid markets
    7:24 – Businesses that are making assets that weren’t investable, investable
                9:11 – Ryan Caldbeck Podcast Episode
    12:03 – Most interesting places where technology is creating investment opportunities
    18:33 – Assets that are likely to tap into new sources of beta
    23:46 – How well are investors prepared for the changes that are coming
    28:35 – Trends in asset management with technology
    33:05 – View on cryptocurrency and blockchain
    36:45 – Places where startups can reduce costs/fees and create efficiencies
    40:17 – Views on private equity markets and their future
    45:40 – Privilege of access problem
    48:50 – Verticals in fintech that are interesting to him
    59:53 – The importance of focus and niche
    1:02:26 – Kindest thing anyone has done for Ben
     
    Learn More
    For more episodes go to InvestorFieldGuide.com/podcast. 
    Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub
    Follow Patrick on twitter at @patrick_oshag

    • 1 hr 5 min

Customer Reviews

sunnydaylei ,

A surprise discovery, not really for investing

This is the best show I’ve discovered recently, thanks to Spotify recommendation. I was suspicious at first since I’m not in the finance world, nor close to investing, VC, banking or any of that, though being in the Bay Area. I’m so glad I gave it a try. The title doesn’t do justice for this show. It’s not the investing 101, how to get a job in finance kind of stuff I was expecting, only much better. The host is such a great listener and questioner - asking all the appropriate questions at the right time, and only that. I could feel that his guest is enjoying the conversation as he is, and as I am. It’s authentic, informative, and just at the right level of detail and intimacy. I envy that he knows so many smart and interesting people and gets to have such nurturing conversations. It’s been a feast, thank you all for sharing. I feel inspired and learned after every episode. I so wish to join a live conversation like this someday myself!

Polmkel ,

Cultivating Conversations | High-Caliber Content

Personal story: After listening to countless episodes, I felt this podcast had earned the right as an “Interest” on my resume. One of the first things my now manger mentioned was this inclusion. He’d just had a friend recommend the podcast to him. I got the job, my first in finance. Appreciate it Patrick.

Official Review: Patrick is a phenomenal communicator and host. After each episode I feel/am a better man for having listened. Regardless of subject (and the variety is brilliant), Patrick and guests never fail to impart high quality wisdom. Have highly recommended and will continue to do just that. Let’s just say, I’m “Interested.”

Slackerville3 ,

Broad Discussions About Finance And Tech

By far the most diverse range of interview topics/guests of any investing podcast. Patrick is great at sitting back and letting his guests do the talking. Random tangential interviews along with deep dives into private businesses, blockchain technology, and Fintech’s future; it’s a joy to start each new podcast. The enjoyable meandering path of the podcast seems to mimics Patrick’s own journey of learning and networking in the investing world.

Top Podcasts In Investing

Listeners Also Subscribed To