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Invest Like the Best

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
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Now displaying: 2020
Dec 3, 2020

My guest today is Zac Bookman. Zac is the Founder and CEO of OpenGov a budgeting and financial management software for local governments. Before he founded OpenGov Zac was an Advisor to U.S. Army General H.R. McMaster in Afganistan, a law clerk on the Ninth Circuit Federal Court of Appeals, and earned a Fullbright Fellowship studying corruption in the Mexican government. This conversation is one of the most unique and wide-ranging of any I've had on the show. We cover how Zac built a world-class sales organization, the power of selling momentum, and the role capital efficiency still plays in building great companies. We also dive into the details on how local government works from mayors down to school board meetings. Please enjoy my conversation with Zac Bookman. 

 

This episode is brought to you by Microsoft for Startups. Microsoft for Startups is a global program dedicated to helping “enterprise-ready” B2B startups successfully scale their companies. If you’re a founder running a B2B company targeting the enterprise, you should definitely check them out. 

  

This episode of Founder’s Field Guide is also brought to you by NetSuite.

Netsuite allows founders to centralize their payment systems, ditch old spreadsheets and Quickbook tools, and finally gain visibility and control over their financials, HR, inventory, eCommerce - all in one place, instantly.

Whether you are doing a million in revenue or hundreds of millions in revenue - see why over 22,000 companies are using NetSuite today. Schedule your free product tour at 
https://www.netsuite.com/invest.

 

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.

Follow Patrick on Twitter at @patrick_oshag

 

Show Notes

(2:56) – (First question) – His career leading up to OpenGov

(5:45) – Experience in Afghanistan and lessons from his time there

(8:54) – Aligning a large group on a strategy

(9:56) – Aligning the team at OpenGov when getting started

(11:54) – Levels of government that matter and what their systems looked like when he was getting started

(15:24) – Role of budget and how money flows in in government operations

(18:55) – How technology can fix the bureaucracy of government

(21:40) – Can technology help the public’s relationship to government

(24:20) – Defining vertical SaaS products

(27:02) – Picking the right products/customers to build your product well

(28:33) – Their purpose when building their first product

(30:23) – Building a company in a highly regulated space

(32:14) – Selling in this space and lessons learned

(34:04) – Building a machine to distribute enterprise software

(37:03) – Getting the technical, political, and commercial processes aligned

(39:40) – Staying up to date on the market and fending off your competition

(42:18) – Competency within public governments

(44:03) – Metrics that he uses to understand the health of OpenGov

(46:07) – The importance of charging the right price for professional services

(48:36) – Hardest episode in developing OpenGov

(50:17) – Valid early criticisms of the company

(52:34) – Advice to new entrepreneurs entering the vertical SaaS space

            (54:06) – The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers

(57:04) – Engineering momentum among teams

(59:00) – Personal improvement as a leader

(1:01:55) – The study of death and why it’s important for him

(1:04:19) – What people can get spending time in the mountains

(1:06:53) – Role of capital efficiency in his work

(1:09:11) – Kindest thing anyone has done for him

 

Learn More

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.

Follow Patrick on Twitter at @patrick_oshag

 

Dec 1, 2020

My guest today is Daniel Gross. Daniel is the founder of Pioneer, an extremely unique company which he describes as a “fully remote startup generator” that helps talented people around the world figure out if their idea has legs. You can learn more about it at pioneer.app. Our wide-ranging conversation covers the art of asking great questions, the use of predictive modeling and psychometrics to identify talent, and why psychometrics are probably overrated and not that scientific. We then dive into exciting new frontiers for tech investing ranging from GPT-3 to satellites. I really enjoyed this conversation and I hope you will too.

 

This episode of Invest like the Best 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 10,000 calls on Square, Snowflake, or almost any company of interest. All you have to do is log in.

Visit https://www.tegus.co/patrick to learn more.

 

This episode of Invest Like The Best is also sponsored by Assure. Assure is changing the way investors manage private transactions.

With Assure, investors can eliminate nearly all the admin cost of private investment. On top of that, they handle all the backend, legal, taxes, accounting, and compliance. All of it, with a straightforward one-time fee. Learn more and try Assure for yourself at https://www.assure.co/patrick.

 

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.

Follow Patrick on Twitter at @patrick_oshag

 

Show Notes

(3:15) – (First question) – His passion for Crank and Whiplash and why movies are great screeners for interviews

(6:15) – Overview of Pioneer

(7:56) – Defining talent

(10:02) – The equivalent page rank when it comes to people

(14:10) – Psychometrics and matter to him

(18:13) – The importance of persistence

(20:23) – The concept of insecure overachievers

(22:48) – Fast twitch vs slow twitch capitalism

(24:31) – Importance of memes as it relates to human behavior today

(26:14) – The landscape of the type of businesses being formed

(29:25) – Overview of GPT3

(33:33) - The Power of Ten Playbook

(38:08) – Technologies going from a frontier to a utility

(42:45) – Why something like a Starlink can’t be regulated

(44:58) – Seed vs leech ratio in capital funding

            (49:10) – Give and Take: Why Helping Others Drives Our Success

(49:15) – Dissecting Patrick’s usual closing question and good questions for screening people

(52:56) – What questions help him get to the bottom of

(55:58) – Kindest thing anyone has done for him

 

Learn More

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.

Follow Patrick on Twitter at @patrick_oshag

 

Nov 26, 2020

My guest today is Emmett Shear, founder and CEO of Twitch. Twitch is the world's leading live streaming platform for gamers, which was acquired by Amazon in 2014. We talk about how Twitch empowers streamers to monetize their audience, the necessity of picking a customer early in a business, and the lessons Emmett learned scaling Twitch from an online reality TV show to a global brand inside Amazon. We also discuss how Twitch has helped create a new language in the internet age with emotes, a topic I am fascinated by. I hope you enjoy this conversation with Emmett Shear.

 

This episode is brought to you by Microsoft for Startups. Microsoft for Startups is a global program dedicated to helping “enterprise-ready” B2B startups successfully scale their companies. If you’re a founder running a B2B company targeting the enterprise, you should definitely check them out. 

 

This episode is also brought to you by Solo Stove. There's simply no better way to create good moments this holiday season than around a fire with a Solo Stove Bonfire.  Complete with 30-day return policy and a lifetime warranty, the unit is made entirely of stainless steel, and at just 20 pounds, the Solo Stove Bonfire is easy to transport for a perfect evening in the backyard, at the campground, or on the beach. Get $5 off with code Patrick5 before December 31st 2020.  

 

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.

Follow Patrick on Twitter at @patrick_oshag

 

Show Notes

(2:52) – (First question) – History of interactive entertainment

(4:10) – Interactivity from the clubs in Vienna and what he learned from that

(5:16) – Origins of Justin.TV and when gaming became the focus for Twitch

(8:59) – What he enjoyed about video streaming games early on

(10:21) – Interactive experience between creators and community

(12:28) – Emotes on twitch and how they came to be

(14:45) – Business of emotes and the affiliates

(16:27) – How these features are proliferating out on the internet and changing it

(17:21) – How far we are in the streamer-influencer phenomenon

(20:00) – Building an effective platform for fans

(23:07) – Evolution of the just chatting piece of Twitch

(24:58) – Favorite parts of Twitch from followers: Chess

(26:45) – Running a business within a larger business

(28:09) – Most interesting trend in the market today

(30:40) – Effective ways for recruiting the team

(31:35) – Most curious about what is happening on the internet today

(33:06) – Advice from the early days of Twitch

            (35:55) – Ira Glass video taste and making things

(36:34) – Focus on strategic mission

(38:06) – Identifying the customer

(40:40) – Starting small

(41:45) – Investors focus on potential market size

(43:00) – Most common reasons talented people fail

(43:47) – Kindest thing anyone has done for him

 

Learn More

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.

Follow Patrick on Twitter at @patrick_oshag

 

Nov 24, 2020

My guests today are Raju Rishi, Nikita Singareddy, and Jason Black of RRE Ventures. RRE is a New York-based VC firm investing in early-stage start-ups with more than 400 investments over its 25 year history. Raju, Nikita, and Jason focus their time in the world of healthcare investing, a topic I haven't explored much personally or on this show. We discuss the current landscape for healthcare investing, the variety of stakeholders in the healthcare value chain, the opportunities for founders and investors in the space, what excites them most about the future of the space, and the impact COVID has had in shaking up the industry. I hope you enjoy my conversation with the RRE team. 

 

This episode is brought to you by Koyfin, one of the fastest growing fintech startups. I discovered Koyfin earlier this year when I asked twitter for the best Bloomberg alternative, and the overwhelming winner was an intriguing new product called Koyfin. 

Koyfin has tons of high-quality data, powerful functionality, and a nice clean interface. If you’re an individual investor, research analyst, portfolio manager, or financial advisor, you should definitely check them out. Sign up for free at koyfin.com

                                                  

Ladder Teams is a modern personal training experience with expertly designed workout plans, 1x1 access to some of the best coaches in the world, and the power of community, all delivered to your phone. 

If you’re looking to switch up your fitness routine at home or if you are back at the gym and looking to refresh your training plan Ladder Teams has a program for you. Check out https://ladder.fit/Patrick to download the app and get started.

 

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.

Follow Patrick on Twitter at @patrick_oshag

 

Show Notes

(2:34) – (First question) – How the team think about attractive investment concepts

(7:13) – The current landscape for healthcare investments

(8:53) – Complications in pricing healthcare and where it needs to change

            (17:45) – Catastrophic Care: Why Everything We Think We Know about Health Care Is Wrong

(17:55) – The major stakeholders and where the innovation is coming from

            (18:22) – The Patient Will See You Now: The Future of Medicine Is in Your Hands

(24:43) – How Covid is changing the healthcare sector

(28:43) – Cutting edge of remote patient monitoring

(37:03) – Passive monitoring and future tech of healthcare

(39:38) – Improving the clinical trial process

(44:54) – Doctors being lost in the shuffle and improving the experience for them

(50:20) – Excites them most about the future of the space

(56:17) – Kindest thing anyone has done for them

 

Learn More

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.

Follow Patrick on Twitter at @patrick_oshag

 

Nov 19, 2020

My guest today is Nick Kokonas, the co-founder of the 3 of the best restaurants and bars in America - Alinea, Next, and The Aviary as well as the co-founder and CEO of Tock, a comprehensive booking system for restaurants. This was one of my favorite conversations in the history of the show. Nick is a philosophy major turned derivatives trader that is now one of the most well-known names in the restaurant and hospitality industry. We cover so many topics I can’t list them here, but I’ll remember it for why it's so important for a business to really know what it's selling and then actually sell it. Nick also pulls back the curtain on why restaurants and even book publishers can be great businesses if you do them in the right way. I felt like this conversation could have gone on for hours and I hope you enjoy it.

 

This episode is brought to you by Microsoft for Startups. Microsoft for Startups is a global program dedicated to helping “enterprise-ready” B2B startups successfully scale their companies. If you’re a founder running a B2B company targeting the enterprise, you should definitely check them out. 

 

This episode is also brought to you by Solo Stove. There's simply no better way to create good moments this holiday season than around a fire with a Solo Stove Bonfire.  Complete with 30-day return policy and a lifetime warranty, the unit is made entirely of stainless steel, and at just 20 pounds, the Solo Stove Bonfire is easy to transport for a perfect evening in the backyard, at the campground, or on the beach. Get $5 off with code Patrick5 before December 31st 2020.  

 

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.

Follow Patrick on Twitter at @patrick_oshag

 

Show Notes

(3:02) – (First question) – Why he thinks it’s so important to own something

(4:35) – Make decisions that have outcomes

(7:00) – His interest in the restaurant business

(8:54) – Why restaurants are so tough

(12:05) – How their business mindset changed their running of the restaurant

(14:35) – Words they would avoid in the restaurant

(16:19) – Asking the right questions in the restaurant business

(20:40) – Importance in taking the right risks

(22:02) – Coming up with innovative strategies for ticketing, selling meals ahead of time, and dynamic pricing

(30:08) – Can dynamic pricing be extended to other businesses

(31:20) – Origin of Tock

(36:17) – Early days of Tock and identifying the right customers/challenges

(41:33) – Importance of the first customer

(44:22) – The typical restaurant business model

(49:23) – Lessons from Tock and the importance of knowing what your selling

(53:47) – Lessons from publishing

(55:44) – Other aspects of business that people know but do nothing about

(1:00:19) – Their response to Covid and lessons learned

(1:07:43) – The real impact to the food delivery companies

(1:09:24) – How businesses communicate their end processes to their customers

(1:14:07) – Kindest thing anyone has done for him

 

Learn More

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.

Follow Patrick on Twitter at @patrick_oshag

 

Nov 17, 2020

My guest today is Niki Scevak, co-founder and partner at Blackbird Ventures. Blackbird is a leading VC firm in Australia and New Zealand and has invested in companies like graphic design platform Canva and autonomous vehicle company Zoox. Our conversation covers the types of wild ideas Blackbird invests in, the landscape of venture and start-ups in Australia and New Zealand, and everything Niki knows about gross margins and customer acquisition. We also introduce a new concept on the show I'm calling Breakdowns, where we dive into a single business, what it does, how it operates, and what makes it tick. I hope you enjoy the conversation.

 

This episode is brought to you by Koyfin, one of the fastest growing fintech startups. I discovered Koyfin earlier this year when I asked twitter for the best Bloomberg alternative, and the overwhelming winner was an intriguing new product called Koyfin. 


Koyfin has tons of high-quality data, powerful functionality, and a nice clean interface. If you’re an individual investor, research analyst, portfolio manager, or financial advisor, you should definitely check them out. Sign up for free at 
koyfin.com

 

This episode of Invest Like The Best is also sponsored by Assure. Assure is changing the way investors manage private transactions. 

With Assure, investors can eliminate nearly all the admin cost of private investment. On top of that, they handle all the backend, legal, taxes, accounting, and compliance. All of it, with a straightforward one-time fee. Learn more and try Assure for yourself at https://www.assure.co/patrick.

 

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.

Follow Patrick on Twitter at @patrick_oshag

 

Show Notes

(2:39) – (First question) – Defining a wild heart

(3:38 – How you identify someone doing their life’s work

(4:30) – Defining a wild idea

(6:13) – Origin of Blackbird and importance of small teams

(7:05) – Investing in companies and not rounds

(09:57) – Signs of a good story and storyteller

(11:37) – Any places he disagrees with the majority of thinkers in the tech investing space

(13:11) – The sleepy firms backing high growth companies

(16:02) – The products of an investment firm

(18:17) – What he likes to see in a startup after their initial investment and gets him worried

(20:21) – Unique characteristics of the New Zealand and Australian markets

(23:36) – Trends he’s seeing in companies he’s backed recently

(24:46) – Everything he knows about gross margins

(25:36) – Range of gross margins in software companies and the quality of the business

(27:00) – Lessons on customer acquisition

(28:23) – Unique way a company acquired customers early on

(29:23) – Customer retention

(31:12) – Finding the best product thinkers

(32:30) – Question he is trying to answer

(34:01) – Lessons from his investing career

(35:40) – Business breakdown of Canva

(38:36) – How Canva gets to its customers

(41:25) – Figuring out the monetization model

(44:42) – Canva’s moat

(46:08) – Most delightful feature

(46:41) – Positive portable lesson from Canva

(49:13) – Best way to learn more about the company

            (49:24) – How I Built This with Melanie Perkins

            (49:27) – This Week in Startups with Melanie Perkins

(49:41) – Kindest thing anyone has done for him

 

Learn More

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.

Follow Patrick on Twitter at @patrick_oshag

 

Nov 12, 2020

My guest today is Todd McKinnon, co-founder and CEO of Okta, the leading provider of identity management for enterprises. Todd started Okta in 2009 after realizing that enterprises would need a robust solution for identity management in a world where everything was quickly moving to the cloud and today counts over 7,000 enterprises as customers. Our conversation focuses on how Todd decided to leave Salesforce to start Okta, the painful early years of growing the business, how companies can create and define a new market, the different roles he's had to play as the company grew and went public, and the frameworks he's put in place to continue to innovate and test new things as public business. I hope you enjoy our conversation.

 This episode is brought to you by Microsoft for Startups. Microsoft for Startups is a global program dedicated to helping “enterprise-ready” B2B startups successfully scale their companies. If you’re a founder running a B2B company targeting the enterprise, you should definitely check them out. 

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.

Follow Patrick on Twitter at @patrick_oshag

 

Show Notes

(2:19) – (First question) – Best slide in his presentation for starting Okta

(5:21) – The early days of Okta and what they were trying to do

(8:36) – Challenge of building the company from an engineering perspective

(10:32) – First version of the Okta product

(11:03) – An overview on identify management

(13:55) – The major innovation in the early days of the product

(16:11) – The early struggles of starting a company

(18:49) – Becoming a default mode solution

(20:39) – Most interesting ways the company has grown its services

(22:10) – Future of platform businesses

(24:24) – Expanding into an infrastructure business

(25:59) – Important shifts that they are paying attention

(28:21) – Future of our digital identity and Okta’s potential role

(32:20) – The chapters of Okta’s story so far

(35:03) – Challenges they had to overcome in growing the company

(37:31) – Recruiting the right talent and fostering it early on

(39:12) – Biggest mistakes he’s made with the business

(41:06) – Benefits of extreme focus vs having a broader view of the problems

(43:35) – Innovating within Okta

(46:02) – How software businesses define cost of revenue and cost of goods

(48:23) – Lessons they’ve learned about selling the services of a small company into the largest company

(49:54) – Lessons from working with bad clients/customers

(51:06) – Their inside view into the future of business today

            (51:10) – Jeff Lawson podcast Episode

(52:36) – Best way to maintain the growth of Okta over the long term

(53:30) – Lessons he would give to business students today

(54:51) – Being scared as a founder

(55:27) – Kindest thing anyone has done for him

 

Learn More

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.

Follow Patrick on Twitter at @patrick_oshag

 

Nov 10, 2020

My guests today are Jason Karp and Rohan Oza. Jason is the founder and CEO of HumanCo, a holding company focused on building businesses that help people live healthier lives. Jason formerly ran the hedge fund Tourbillon Capital and was an audience favorite when he was on the podcast several years ago. Rohan is the co-founder of CAVU Venture Partners, one of the fastest-growing venture funds in the CPG space. Before Cavu, Rohan focused on supercharging brands like Vitaminwater and Smartwater at Glaceau which was acquired by Coca Cola for over $4b dollars. You may also recognize his name as a recurring Shark on ABC's Shark Tank. Our conversation covers how to think about investing in brands, what makes for a great brand, how partnerships with influencers and celebrities can turbocharger a brand,  how brand ultimately gives you pricing power, and how Rohan and Jason try to add, in their words, sizzle, to the brands they work with. I really enjoyed this conversation with two of the smartest people I know on brands and brand strategy and hope you will too. 

 

This episode is brought to you by Koyfin, one of the fastest growing fintech startups. I discovered Koyfin earlier this year when I asked twitter for the best Bloomberg alternative, and the overwhelming winner was an intriguing new product called Koyfin. 

Koyfin has tons of high-quality data, powerful functionality, and a nice clean interface. If you’re an individual investor, research analyst, portfolio manager, or financial advisor, you should definitely check them out. Sign up for free at koyfin.com

 

Ladder Teams is a modern personal training experience with expertly designed workout plans, 1x1 access to some of the best coaches in the world, and the power of community, all delivered to your phone. 

If you’re looking to switch up your fitness routine at home or if you are back at the gym and looking to refresh your training plan Ladder Teams has a program for you. Check out https://ladder.fit/Patrick to download the app and get started.

 

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.

Follow Patrick on Twitter at @patrick_oshag

 

Show Notes

(2:58) – (First question) – Exploring the early part of Rohan’s career with Mars

(4:53) – First time changing a brand’s image

(6:40) – Jason’s transition since his last appearance on the podcast

(9:47) – What parts of a brand excite Rohan as an investor

(11:33) – The marketing machine once you find a brand

(13:13) – Options in the retail strategy

(19:07) – Biggest errors early in a brands lifecycle

(21:04) – The shift where consumers care more about the makeup of a product than just the brand

(26:20) – Finding the fanatical few in the early part of a brands lifecycle

(31:03) – How the role of celebrity has changed in shaping brands

(33:01) – The importance of how a brand makes consumers feel

(36:15) – Will distribution drive market changes in the future

(38:17) – Driving revenue multiples for products

(48:33) – Categories in health and wellness ripe for disruption

(52:20) – How scalable health and wellness brands are as public companies

(55:00) – Challenges that older brands have in today’s environment

(56:46) – Kindest thing anyone has done for Rohan

 

Learn More

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.

Follow Patrick on Twitter at @patrick_oshag

 

Nov 5, 2020

My guest this week is John Chambers. John was the CEO of Cisco from 1995 to 2015 where he helped grow Cisco from $70 million to $40 billion in annual revenue. In this conversation we discuss the best business lesson he learned from long time GE CEO Jack Welch, his key lessons from acquiring over 180 companies with Cisco, pattern recognition and playbooks, capitalizing on market transitions enabled by new technologies, the value of team offsites, and a lot more. I was immediately drawn into John's magnetic personality and it's easy to see how he was so adept at running a 40,000 person company for 2 decades. I hope you enjoy this great conversation with John Chambers.

This episode is brought to you by Microsoft for Startups. Microsoft for Startups is a global program dedicated to helping “enterprise-ready” B2B startups successfully scale their companies. If you’re a founder running a B2B company targeting the enterprise, you should definitely check them out. 

 This episode is also sponsored by Vanta.  Vanta has built software that makes it easier to both get and maintain your SOC 2 report, at a fraction of the normal cost. Founders Field Guide listeners can redeem a $1k off coupon at vanta.com/patrick

 

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.

Follow Patrick on Twitter at @patrick_oshag

 

Show Notes

(2:04) – (First question) – Why companies need a near death experience

(6:37) – The way his leadership changed between 1999 and 2003

(11:34) – His career before and leading to his time joining Cisco

(17:51) – What Cisco was like when he joined

(21:02) – Role that pattern recognition plays in his management

(24:16) – Lessons learned from the spate of acquisitions they took on under his tenure

(30:46) – Pricing deals and using Cisco’s scale to be successful

(33:09) – Lessons he learned in terms of distribution

(35:10) – What he learned from his relationship with Shimon Peres

(42:08) – His role in helping young entrepreneurs

(46:00) – Transformation on his team building trips to Alaska

(50:42) – Transitions in the world he is focused on right now

(52:542) – Kindest thing anyone has done for John

 

Learn More

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.

Follow Patrick on Twitter at @patrick_oshag

 

Nov 3, 2020

My guest this week is Anu Hariharan. Anu is a partner at Y-Combinator's Continuity Fund where she focuses on growth investing. Before YC, Anu was an Investment Partner at Andreesen Horowitz where she worked with portfolio companies Airbnb, Instacart, Medium and Udacity. In this conversation, we discuss growth stage businesses and their business models, how her background as an engineer impacts her investing style, the most interesting international markets for tech start-ups, and how much opportunity there still is for investing in tech and e-commerce startups. This conversation left me thinking about how much digital transformation there still is in front us and the exciting opportunities ahead. Enjoy this great conversation with Anu Hariharan. 

 

This episode is brought to you by Koyfin, one of the fastest growing fintech startups. I discovered Koyfin earlier this year when I asked twitter for the best Bloomberg alternative, and the overwhelming winner was an intriguing new product called Koyfin. 


Koyfin has tons of high-quality data, powerful functionality, and a nice clean interface. If you’re an individual investor, research analyst, portfolio manager, or financial advisor, you should definitely check them out. Sign up for free at 
koyfin.com

 

 This episode of Invest Like The Best is also sponsored by Assure. Assure is changing the way investors manage private transactions. 

With Assure, investors can eliminate nearly all the admin cost of private investment. On top of that, they handle all the backend, legal, taxes, accounting, and compliance. All of it, with a straightforward one-time fee. Learn more and try Assure for yourself at https://www.assure.co/patrick.

 

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.

Follow Patrick on Twitter at @patrick_oshag

 

Show Notes

(2:45) – (First question) – How she thinks about growth stage businesses through their business models

(5:00) – Her views on the winner-take-all business goal

(9:53) – How to prioritize the stakeholders when building a network business

(12:19) – Priorities in growth stage businesses vs those seeking Series A funding

(18:25) – Most interesting international markets

(21:44) – Risks in investing in international tech startups

(24:54) – Assessing a hardware-based tech company vs software business

(30:22) – How her background as an engineer impacts her investing style

(36:11) – Lessons from the various growth strategies she’s observed

(40:05) – How valuation impacts the company and her decision to invest

(45:45) – How far along are we into the global digital transformation and what opportunity is left

(48:15) – Sectors that are still primed for more digital transformation

(52:50) – How the tech investing landscape has changed during her career

(57:45) – Kindest thing anyone has done for her

 

Learn More

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.

Follow Patrick on Twitter at @patrick_oshag

 

Oct 29, 2020

My guest today is Laura Behrens Wu, co-founder and CEO of Shippo. Shippo started in 2014 after Laura realized with her own e-commerce start-up that shipping was an incredibly difficult task for most merchants, so she set out to fix the problem for everyone. Shippo let's merchants small and large use its dashboard or APIs to simplify the shipping and tracking process. Our conversation focuses on Laura's background prior to Shippo, how Shippo's business and business strategy have evolved, the inherent challenges of building a shipping platform, and the intersection of the physical and digital worlds. I hope you enjoy our wide-ranging conversation.

 

This episode is brought to you by Microsoft for Startups. Microsoft for Startups is a global program dedicated to helping “enterprise-ready” B2B startups successfully scale their companies. If you’re a founder running a B2B company targeting the enterprise, you should definitely check them out. 

 

This episode is also sponsored by Vanta.  Vanta has built software that makes it easier to both get and maintain your SOC 2 report, at a fraction of the normal cost. Founders Field Guide listeners can redeem a $1k off coupon at vanta.com/patrick

 

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.

Follow Patrick on Twitter at @patrick_oshag

 

Show Notes

(2:57) – (First question) – The story of Popout and how it led to Shippo

(7:40) – Challenge of working in a huge and crowded market

(10:36) – How Shippo changed shipping for small businesses

(12:30) – First big break in their favor

(13:39) – Their master account with the major shipping companies

(14:39) – Why is the shipping industry so complex

(16:25) – Most painful part of building Shippo

(18:20) – Advice for people in early company building

(19:26) – Pricing software in early days

(20:32) – The early days of Shippo and getting it to where it is today

(23:17) – Going to market and targeting new customers when they’re mostly small businesses

(25:48) – Partnering with a larger company, in their case Shopify

(27:52) – How they think about their long-term planning

(30:48) – Competing in a world where companies can own their own infrastructure

(32:39) – How often they think about other competitive advantages

(34:20) – Worst question an investor asked her: what if Amazon tries to copy them

(35:17) – Her superpowers as a founder

(36:41) – API vs dashboard and the difference in their customer bases

(38:52) – What businesses that need shipping today need to know

(40:14) – Changes in how businesses are being built today

(41:28) – What excites her most about the future of this business

(43:28) – Kindest thing anyone has done for her

 

Learn More

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.

Follow Patrick on Twitter at @patrick_oshag

 

Oct 27, 2020

My guests today are Rich Barton and Brad Gerstner. Brad is the founder of Altimeter Capital and is one of my favorite active investors. Brad and Altimeter were one of the largest investors in Snowflake in its earlier days and continue to invest in iconic modern businesses with an extreme focus. Rich has one of the most impressive resumes in the business world. He founded Expedia, Glassdoor, and Zillow; He’s a longtime Netflix board member, since before they went public; he’s a venture partner at Benchmark Capital; and he give back through the Barton family foundation. Our conversation covers Rich’s “power to the people,” strategy, Brad and Rich’s perspectives on taking companies public through SPACs vs. IPOs, and their perspectives on how to build a great company. This one is so fun, we even discuss how to come up with company names, talk about the importance Wizard of Oz, and explore the importance of big hairy audacious goals. I really enjoyed this conversation with two of the smartest people I know, and I hope you will too.

 

This episode is brought to you by Koyfin, one of the fastest growing fintech startups. I discovered Koyfin earlier this year when I asked twitter for the best Bloomberg alternative, and the overwhelming winner was an intriguing new product called Koyfin. 

Koyfin has tons of high-quality data, powerful functionality, and a nice clean interface. If you’re an individual investor, research analyst, portfolio manager, or financial advisor, you should definitely check them out. Sign up for free at koyfin.com

 

This episode of Invest Like The Best is also sponsored by Assure. Assure is changing the way investors manage private transactions.

With Assure, investors can eliminate nearly all the admin cost of private investment. On top of that, they handle all the backend, legal, taxes, accounting, and compliance. All of it, with a straightforward one-time fee. Learn more and try Assure for yourself at https://www.assure.co/patrick.

 

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.

Follow Patrick on Twitter at @patrick_oshag

 

Show Notes

(2:59) – (First question) – How Brad and Rich met

(5:57) – The instant click between them

(7:21) – The power to the people perspective

            (7:29) – Brad Gerstner Podcast Episode

(10:21) – Delivering information to consumers

(11:31) – The investing perception of data-delivery businesses

(13:54) – How they use SPACs

(17:38) – How entrepreneurs view SPACs

(20:17) – Lessons from their involvement in Altimeter Growth Corp

(23:57) – Defining value add investor in the public and private markets

(26:36) – The Wizard of OZ and Pygmalions

(30:41) – Leadership mold at businesses and big audacious goals

            (30:44) – No Rules Rules: Netflix and the Culture of Reinvention

(36:05) – Frank Slootman’s leadership style

            (36:12) – Amp It Up

            (46:13) – TAPE SUCKS: Inside Data Domain, A Silicon Valley Growth Story

(38:11) – Courage in leadership

(41:33) – Physical businesses vs digital only businesses

(43:34) – Getting companies fit

(45:39) – Lessons around talent density

(48:28) – State of the world and markets today since the inception of the pandemic

(53:46) – Making up words for companies and fertile ground

(56:45) – Go to market model vs business model

(58:50) – Early days of product market sales

(1:03:03) – Advice to early investors and entrepreneurs for the future of their careers

(1:08:10) – The board challenge

(1:12:06) – What question are they working hard to answer right now

(1:16:09) – Kindest thing anyone has done for Rich

 

Learn More

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.

Follow Patrick on Twitter at @patrick_oshag

 

Oct 22, 2020

My guest today is Jason Citron, founder and CEO of Discord. Discord is one of the largest and fastest growing social networks in the world. It started as a place for gamers to congregate online, but thanks to how easy it makes it to create a community of any type and its offering of text, audio, and video as means of communication, it has expanded far beyond gaming. It has the potential to become the default digital “third place” that we go to find belonging in a variety of online communities. With over 100 million users, it’s also one of the most interesting communications service businesses since the original social networks rose to power.

Our conversation focuses on his background prior to Discord, Discord’s founding and growth, its business model and how it has evolved over the past 8 years, and what the future holds for Discord. As we talked, I had this sense that I’d be willing to go work for Jason, and I think you’ll see why. I hope you enjoy our wide ranging conversation.

 

This episode is brought to you by Microsoft for Startups. Microsoft for Startups is a global program dedicated to helping “enterprise-ready” B2B startups successfully scale their companies. If you’re a founder running a B2B company targeting the enterprise, you should definitely check them out. 

 

This episode is also sponsored by Vanta.  Vanta has built software that makes it easier to both get and maintain your SOC 2 report, at a fraction of the normal cost. Founders Field Guide listeners can redeem a $1k off coupon at vanta.com/patrick

 

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.

Follow Patrick on Twitter at @patrick_oshag

 

Show Notes

(3:17) – (First question) – Lessons from his time as a video game developer

(7:58) – Going from game developer to game development platform

(12:23) – From his first startup to Discord

(16:33) – Expressing the hypothesis of discord

(20:10) – How to know what signal to build upon

(22:11) – Early adoption of Discord

(26:17) – Getting the word out about Discord in the early days

(30:43) – Creating more than just a platform, but creating a third place for people to congregate

            (32:38) – The Great Good Place: Cafes, Coffee Shops, Bookstores, Bars, Hair Salons, and Other Hangouts at the Heart of a Community

(32:55) – The evolution and expansion of the types of community using their platform

(37:27) – Discord’s business model and how it’s evolved

(41:32) – Enhancing communication through Nitro

(45:05) – Big principles for company building at Discord

(51:22) – His thoughts around competitive advantage for the platform

(52:55) – Creating a holistic experience for the users

(55:45) – What bothers him the most when hiring

(57:47) – Kindest thing anyone has done for him

Learn More

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.

Follow Patrick on Twitter at @patrick_oshag

 

Oct 20, 2020

My guests today are Ben Gilbert and David Rosenthal. Ben and David are investors but also the duo behind the Acquired podcast, which is one of my favorite podcasts that dives deep into business history and famous acquisitions. I recommend you check it out.

In this conversation, we review of some of the greatest corporate acquisitions of all time and also discuss investing lessons Ben and David have learned across their careers. I hope you enjoy my conversation with Ben and David.

 

This episode is brought to you by Koyfin, one of the fastest growing fintech startups. I discovered Koyfin earlier this year when I asked twitter for the best Bloomberg alternative, and the overwhelming winner was an intriguing new product called Koyfin. 

Koyfin has tons of high-quality data, powerful functionality, and a nice clean interface. If you’re an individual investor, research analyst, portfolio manager, or financial advisor, you should definitely check them out. Sign up for free at koyfin.com

 

This episode of Invest Like The Best is also sponsored by Assure. Assure is changing the way investors manage private transactions.

 With Assure, investors can eliminate nearly all the admin cost of private investment. On top of that, they handle all the backend, legal, taxes, accounting, and compliance. All of it, with a straightforward one-time fee.

Learn more and try Assure for yourself at https://www.assure.co/patrick.

 

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.

Follow Patrick on Twitter at @patrick_oshag

 

Show Notes

(2:29) – (First question) – What they look for in new founders based on more experienced managers they’ve worked with

(5:07) – Difference between emerging vs legacy market

(9:17) – Research steps to determine if a market can get big enough to invest in

(12:08) – Working with other firms for doing an initial investment round

(15:42) – Recent trends in the supply of capital and number of founders in the VC space

(18:56) – Lessons they have learned studying corporate transactions

(24:13) – How do startups transform once they are acquired to increase their multiples so much

(28:10) – What they learned from deliberations that take place within the acquiring company

(30:39) – Most interesting deal for them to unpack

(32:44) – What are features of a business that is difficult for others to replicate

(35:52) – Any company that are intimidated to go up against

(37:37) – Who would they follow

            (38:52) – Blake Robbins Podcast Episode

(39:09) – Missing pieces in their skill set

(41:43) – Early green shoots

(44:40) – Lessons from Alaska Airlines acquisition and the value of scarcity

(47:07) – Kindest thing anyone has done for them

 

Learn More

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.

Follow Patrick on Twitter at @patrick_oshag

 

Oct 15, 2020

My guest today is Leore Avidar. Leore is the co-founder and CEO of Lob, a company which makes it easy to send direct mail programmatically. He’s also the founder of a new company focusing on sports card collectibles, Alt, which is how we originally connected. Our conversation ranges from building Lob, buying a Lebron James rookie card, starting a 2nd business while operating his first and how Leore tries to create and sell superpowers. Like my conversation with Rahul Vohra from Superhuman, I think this conversation will inspire entrepreneurs out there to start building aggressively. Please enjoy.

 

This episode is brought to you by Microsoft for Startups. Microsoft for Startups is a global program dedicated to helping “enterprise-ready” B2B startups successfully scale their companies. If you’re a founder running a B2B company targeting the enterprise, you should definitely check them out. 

 

This episode is also sponsored by Vanta.  Vanta has built software that makes it easier to both get and maintain your SOC 2 report, at a fraction of the normal cost. Founders Field Guide listeners can redeem a $1k off coupon at vanta.com/patrick

 

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.

Follow Patrick on Twitter at @patrick_oshag

 

Show Notes

(2:55) – (First question) – Origin of Lob

(6:14) – Creating and selling superpowers to other people and its value proposition

(7:23) – Defining an API in his words

(8:44) – Early breaks for Lob

(10:45) – Early lessons in responsible growth

(12:19) – Physical infrastructure behind Lob

(14:14) – Surprises in mail delivery

(15:00) – Progression through their pricing models

(18:10) – Leaders in the world of making the world programmable

(19:07) – Their interest in the physical world

(19:45) – Hardest part of scaling a physical business

(21:09) – Building a culture that keeps people around

(23:13) – Why he is fascinated by negotiations and what he’s learned from it

(25:20) – Scarcity, time, and leverage impact’s on negotiations

(26:35) – His interest in collectibles and the formation of Alt

(30:18) – Size of the alternative market he focuses on

(30:54) – The focus on cards

(32:18) – An overview of collectible cards industry

(33:19) – What is the API of card collection and trading

(35:51) – Competitors in the space

(37:19) – Buying a Lebron James card

(38:21) – Building a fund around the collectibles and the strategy

(39:45) – What it means to be a technology company

(40:23) – Collectibles beyond sports

(41:30) – Defining a good investor

            (43:32) – Thinking in Bets: Making Smarter Decisions When You Don't Have All the Facts

(43:43) – Qualities he looks for in investors

(45:03) – What does the collectible universe look like over the next 5-7 years

(45:43) – Cultural value of assets

(48:50) – Managing his time while launching two businesses

(49:51) – What he’s most excited about over the next 6 months

(51:45) – Consolidation of API businesses

(52:19) – Kindest thing anyone has done for him

 

Learn More

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.

Follow Patrick on Twitter at @patrick_oshag

 

Oct 13, 2020

My guest today is Jacqueline Novogratz. Jacqueline is the founder and CEO of Acumen, a non-profit global venture fund that uses entrepreneurial approaches to solve the problems of poverty.  Our conversation touches on how Jacqueline left Wall Street and ended up starting a micro finance bank in Rwanda, how she thinks about investing in character, how creating dignity plays such a major role in her investments, and how governments and businesses can work together to solve the world's toughest problems. It is a bit of a departure from my normal investing conversations but contains powerful lessons for many investors and builders. I really enjoyed our conversation and hope you will to. 

 

This episode of Invest Like The Best is sponsored by Canalyst. Canalyst is the leading destination for public company data and analysis. 

If you’re a professional equity investor and haven’t talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick.  

 

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.

Follow Patrick on Twitter at @patrick_oshag

 

Show Notes

(2:29) – (First question) – Where the concept of the blue sweater came from for her book.

            (2:44) - The Blue Sweater: Bridging the Gap Between Rich and Poor in an Interconnected World

(4:29) – Every child has a humiliated experience and the impact on their life

(6:55) – The origin of Acumen

(10:42) – Why character is such an important investing filter for her

(11:59) – How the markets have changed through the lens of Acumen

(16:59) – The challenges of getting started

            (17:04) – Manifesto for a Moral Revolution: Practices to Build a Better World

(19:46) – Embracing the idea of being uncomfortable and an example for her

(21:50) – The space between government action and market action

(26:11) – The concept of conformity traps

(29:29) – The lens of moral imagination

(30:32) – The importance of brining dignity to others

(35:09) – Entrepreneurial skills she sees outside of the US that we lack here

(39:38) – Biggest problems across the globe she is interested in tackling

(42:48) – Impediments to investing in global problems

(49:11) – Kindest thing anyone has done for her

 

Learn More

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.

Follow Patrick on Twitter at @patrick_oshag

 

Oct 8, 2020

My guest today is Justin Singer, the founder and CEO of Caliper Foods and Stillwater Brands, two leading companies in the cannabis industry. We start our conversation with a fascinating discussion on how regulation creates or destroys business and investing opportunities, and then go on to discuss the ins and outs of the cannabis industry in detail. You’ll be able to tell quickly how high-quality Justin is as a thinker and operator, and you’ll learn a ton about this nascent business. Please enjoy our conversation.

 

This episode is brought to you by Microsoft for Startups. Microsoft for Startups is a global program dedicated to helping “enterprise-ready” B2B startups successfully scale their companies. If you’re a founder running a B2B company targeting the enterprise, you should definitely check them out. 

 

This episode is also sponsored by Vanta.  Vanta has built software that makes it easier to both get and maintain your SOC 2 report, at a fraction of the normal cost. Founders Field Guide listeners can redeem a $1k off coupon at vanta.com/patrick

 

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.

Follow Patrick on Twitter at @patrick_oshag 

Show Notes

(2:51) – (First question) – How changes in regulation create market opportunities

(5:38) – Why VC’s need to pay attention to regulatory changes

(6:50) – Story of Section 230 of the communication decency act

(8:54) – Relationships between rules, laws, and free markets

(11:56) – How regulatory changes impacted recent business ventures

(13:30) – His initial interest in the cannabis space

(17:28) – How the industry participants have changed over time

(21:04) – An overview of the cannabis industry and different pieces of the chain

(25:51) – What has led to delays in the legalization of the marijuana industry

(28:52) – How the dosage of the product impacts the business

(31:34) – CBD vs THC industry differences

(32:53) – How much of this industry is left to be unlocked and potential timing

(35:55) – Business and investing opportunities in the space

(38:16) – Competitive frontier in cannabis

(40:37) – The timeline and pending changes coming

(43:03) – Margins and business factors of his business

(45:51) – First big break for the business

(49:47) – What he learned working under Tim Wu

(50:34) – Why we are in the golden error for fraud

(52:11) – Avoiding fraud

(55:12) – What he wants to learn more about in the cannabis space

(56:50) – Kindest thing anyone has done for him

Learn More

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.

Follow Patrick on Twitter at @patrick_oshag

 

Oct 6, 2020

My guest today is Jesse Livermore. I’ve worked with Jesse as part of our research partners program at O’Shaughnessy Asset Management for years now. Whenever there is a huge, important, and complex issue to be studied, I believe he’s among the best minds in the world to tackle it. He did that recently on the topic of what he calls “upside down markets,” which is the topic of this conversation. We seek to answer the simple question: against a horrible economic backdrop, how can the stock market be near all-time highs? Jesse explains in detail the impact that fiscal policy has had on the market and may have in the future. Please enjoy this master class in upside down markets.

 

This episode of Invest Like The Best is sponsored by Canalyst. Canalyst is the leading destination for public company data and analysis. 

If you’re a professional equity investor and haven’t talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick.  

 

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.

Follow Patrick on Twitter at @patrick_oshag

 

Show Notes

(2:29) – (First question) – What is Upside Down Markets

(5:44) – Overview on monetary easing and the fed’s role in the markets

(9:42) – Why fiscal policy is such an important lever and the impact it has on the economy

(15:07) – The impact of stimulus on public companies’ fundamentals

(19:25) – The mix of assets in the market due to stimulus

(22:13) – What made 1929 so different to how we are reacting today

(26:14) – Negative concerns: too much money in the system and the risk of inflation

(32:43) – Will the pendulum swing back to labor and higher wages

(37:23) – How these changes could impact specific companies or sectors differently

(41:34) – How he is applying all of this to his personal investment philosophy

(44:25) – Biggest risks still out there

(49:51) – Most interesting gap in his knowledge putting together this piece

 

Learn More

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.

Follow Patrick on Twitter at @patrick_oshag

 

Oct 1, 2020

Today’s episode represents a new chapter for Invest Like the Best, so requires a longer introduction than normal. Starting today, I’ll be bringing you two episodes per week on the same feed. On Tuesday’s, I’ll focus on investors, and on Thursday’s, I’ll host builders—founders, CEOs, and operators from all different fields. We call this new Thursday series Founder’s Field Guide. There’s nothing more interesting to me than how great businesses get build, and how investors can identify those businesses at the right time. We’ve already recorded with founders build companies in food, technology, infrastructure, shipping, collectibles, and many more categories. The goal each weak will be to have a builder share what they’ve done, how they’ve done it, and what they’ve learned along the way. We view this as a critical next step in furthering our mission: to capture and openly share the world’s best knowledge on business and investing.

Onto the kickoff episode with Rahul Vohra. Rahul is the Founder & CEO of Superhuman, an extremely popular product for managing email. Rahul describes himself as a Computer Scientist, Gamer, Entrepreneur, and Designer. You’ll see quickly why it’s the intersection of these areas that sets Superhuman apart. We discuss why emotion matters when building products, and how other entrepreneurs can learn from his experience. Please enjoy the very first episode of Founder’s Field Guide, and stay tuned in future weeks as we host leaders from Nike, Cisco, Twitch, and so many more…listen in as we explore the world of cannabis, baking (not that kind), manufacturing, hardware, software, and more. Let’s dive in.

 

This episode is brought to you by Microsoft for Startups. Microsoft for Startups is a global program dedicated to helping “enterprise-ready” B2B startups successfully scale their companies. If you’re a founder running a B2B company targeting the enterprise, you should definitely check them out. 

 

This episode is also sponsored by Vanta.  Vanta has built software that makes it easier to both get and maintain your SOC 2 report, at a fraction of the normal cost. Founders Field Guide listeners can redeem a $1k off coupon at vanta.com/patrick

 

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.

Follow Patrick on Twitter at @patrick_oshag

 

Show Notes

(3:56) – (First question) – His interest in game design and emotion in software creation

(5:15) – Key elements of game design

(6:23) – Toys in digital software creation

(8:48) – Finding success in boring software solutions

(11:19) – Getting confidence while building when there are no real customers

(14:08) – How they landed on their final product

            (15:40) – The Superhuman Product/Market Fit Engine

(20:46) – Determining software price

            (21:55) – Positioning Your Startup is Vital — Here’s How to Nail It

            (23:09) – Positioning: The Battle for Your Mind

            (24:13) – Monetizing Innovation: How Smart Companies Design the Product Around the Price

(26:36) – First big break for the business

(29:04) – How technology companies actually grow

(32:15) – Branding a software

(33:57) – How he evaluates a company brand as an investor

(36:07) – Questions to ask founders when considering an investment

(37:35) – How the distribution of Superhuman worked so well

(41:25) – Most common question asked by VC’s about Superhuman

(43:00) – Why they do manual onboarding of customers

            (43:05) – Daniel Ek Podcast Episode

(45:10) – Cost structure of a busines looking to reach the billion-dollar valuation

(47:18) – Designing for flow in software business

(51:21) – His design philosophy and their joy formula  

(58:03) – His superpower

(1:00:46) – The power of therapy

(1:02:50) – Why he invests in other companies

(1:05:05) – Trends in the technology space that have him excited

(1:07:28) – The future for Superhuman

(1:10:26) – Kindest thing anyone has done for him  

 

Learn More

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.

Follow Patrick on Twitter at @patrick_oshag

 

Sep 29, 2020

Before getting to this week’s guest, an announcement: starting Thursday we will be introducing a new series of interviews. Be sure to check this same podcast feed in two days to learn more.

My guest this week goes by the pseudonym Modest Proposal. He’s both a close friend, and one of the most respected thinkers on financial twitter. I field more inbound questions about him than just about anyone, and you’ll see why in this episode. We discuss many of the biggest themes in today’s stock market, from consumer to technology to marketplace and local home services. As always, Modest brings specific insight and general frameworks to the discussion. I talk to him as often as I can because I learn something new every time, and this discussion was no exception. Please enjoy my conversation with Modest Proposal.

 

This episode of Invest Like The Best is sponsored by Canalyst. Canalyst is the leading destination for public company data and analysis. 

If you’re a professional equity investor and haven’t talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick.  

 

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.

Follow Patrick on Twitter at @patrick_oshag

 

Show Notes

(2:37) – (First question) – How investing is about underwriting the future

(5:42) – Essential tools to underwrite the future

            (7:59) – Michael Mauboussin base rate book

(9:02) – Increasing returns to scale as the most important tool

(11:36) – Example of silly investments

(14:00) – Ideas of consumer signal and non-linear beahvior

(16:30) – Why he was blown away by ibuyer.com

(19:08) – How businesses are targeting facilitating transactions

(23:11) – Ecommerce and digital penetration in business

            (25:42) – Gavin Baker podcast episode

            (26:00) – Modest proposal last podcast appearance

(27:56) – His thoughts on the extinction of so many businesses as a result of the pandemic

(32:26) – Chart tracking Product to service against homogeneous to heterogenous

            (33:41) – The Perfect Store

            (33:49) – eBoys

(43:51) – Other features of business that fascinate him

(46:29) – Ideas that pique his interest right now

(51:20) – Case study: IAC/InterActiveCorp

(59:36) – Barry Diller’s superpowers

(1:01:17) – Why he’s spent so much time exploring IAC/InterActiveCorp

(1:02:56) – Related companies to explore

Learn More

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.

Follow Patrick on Twitter at @patrick_oshag

 

Sep 22, 2020

My guest this week is Lauren Taylor Wolfe. Lauren is the co-founder and Managing Partner of Impactive Capital. Prior to founding Impactive she spent 10 years at Blue Harbour Group, a $3 billion activist investment firm. Our conversation is on the modernization of the activist investor playbook—how investors engage with companies to make them better and improve long term outcomes. We discuss the entire activist toolkit, focuses on what has changed the most in recent years.

I’m also very excited to announce a new initiative. After years of building, operating, and investing in software, we are launching Positive Sum, a new early stage equity investing firm. You can read a bit more at positivesumadvisors.com. Now, please enjoy my conversation with Lauren Taylor Wolfe.

 

This episode of Invest Like The Best is sponsored by Canalyst. Canalyst is the leading destination for public company data and analysis. 

If you’re a professional equity investor and haven’t talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick.  

 

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.

Follow Patrick on Twitter at @patrick_oshag

 

Show Notes

(2:31) – (First question) – Her background and how she landed at Impactive Capital

(6:25) – Impactive’s strategy vs the stereotype of the activist investor

(10:55) – Potential candidates for what they do

(13:26) – How they view the small cap tech world as the space is dominated by huge companies

(15:24)  - How capital allocation has evolved over her career

            (15:30) - The Outsiders: Eight Unconventional CEOs and Their Radically Rational Blueprint for Success

(17:38) – Best capital allocation strategies and mistakes that most companies make

(18:48) – The levers activists pull: cap structure; capital allocation and operating structure

(22:00) – Major lessons from earlier in her career

(23:25) – Major changes in Governance as part of the ESG strategy

(26:13) – The issue of dual-class in the space

(27:35) – Features of a pristine healthy board

(28:40) – Board’s role setting incentives and objectives for management

(29:55) – How she thinks about the E&S in ESG and how it helps shareholders

(32:56) – Applying her strategy in a real-world example

(37:40) – What they look for in a business when it comes to sum of the parts

(40:29) – Businesses that are misunderstood and what she looks for in that category

(41:39) – How she manages relationships with the boards

(45:11) – What she has learned transitioning business models

(47:08) – The rise of employee activism

(50:02) – What she’s seeing in terms of diversity and inclusion in board rooms and C-Suites

(53:32) – Best practices and ways to disrupt hiring

(57:48) – Something she doesn’t understand well today that she wishes she did

(58:59) – Kindest thing anyone has done for her

 

Learn More

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.

Follow Patrick on Twitter at @patrick_oshag

Sep 15, 2020

My guest today is Rory Sutherland. Rory is the Vice Chairman of Ogilvy & Mather Group, which is one of the largest and most renowned advertising agencies in the world. He’s also the author of one of my favorite recent books called Alchemy: The surprising power of ideas that don’t make sense. In this conversation, we explore many of his counterintuitive ideas about business. Rory makes you think as much as anyone, so I hope you enjoy this conversation.

 

This episode of Invest Like The Best is sponsored by Canalyst. Canalyst is the leading destination for public company data and analysis. 

If you’re a professional equity investor and haven’t talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick.  

 

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.

Follow Patrick on Twitter at @patrick_oshag

 

Show Notes

(2:12) – (First question) – Why spreadsheets and logic kill magic

(5:42) – What a product/service is vs how it’s delivered and makes people feel (regular moonshot vs psychological moonshot)

(13:22) – Psychological anomalies - doing things faster, better, cheaper (Red Bull vs Coke)

(19:54) – Swiss army knife that companies should avoid

(22:50) – Don’t design for average

(24:39) – How do people approach improving their business through marketing

(27:30) – Case for direct mail

(29:22) – Turning your weaknesses into a strength

(34:29) – The seven deadly sins and how useful they are as guideposts

(37:38) – Most powerful sin for marketing

(39:14) – Reaching intelligent answers from dumb questions

(43:25) – Why the opposite of a good idea can sometimes be a good idea

(47:30) – Kindest thing anyone has done for him

 

Learn More

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.

Follow Patrick on Twitter at @patrick_oshag

Sep 8, 2020

My guest this week is Michael Seibel. Michael is a Partner at Y Combinator, and the CEO of YC's startup accelerator. He was the cofounder and CEO Justin.tv, which eventually became Twitch, and Socialcam. In this conversation, we discuss all Michael has learned reviewing thousands of applications to YC, interviewing countless new entrepreneurs, and watch young companies begin to grow and, occasionally, find product market fit. Listeners will also enjoy when Michael traps me big time in my thinking about AirBnb and his framework for great problems to solve. Enjoy this great conversation with Michael Seibel

 

This episode of Invest Like The Best is sponsored by Canalyst. Canalyst is the leading destination for public company data and analysis. 

If you’re a professional equity investor and haven’t talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick.  

 

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.

Follow Patrick on Twitter at @patrick_oshag

 

Show Notes

(2:22) – (First question) – Emerging trends among founders

(6:00) – The long-term impact of Covid on business

(7:16) – What an application to YC looks like and what stands out for him

(11:46) – What he wants to learn in the interviews

(13:54) – Poise in the interviews

(15:40) – How the YC experience has evolved and improvements they’ve made

(18:38) – How he defines technology

            (18:50) – Every Company is Becoming a Software Company

(21:12) – His thoughts on non-software companies and how they play into what YC does

(23:48) – Why frequency and intensity of the problem matter to him

(28:32) – Serving the supplier and building the demand

(30:38) – Bravery in founders

(36:07) – Partnerships and collaboration in venture capital investing

(37:58) – Second time founders focus on distribution

(39:23) – Coaching the psychological component of being a founder

(44:16) – Learning as a founder vs the education system

(46:08) – Customer vs investor focus of founders’ mindset

(48:16) – How teams know they are really onto something

(52:38) – His being a founder trainable or innate

(54:08) – Kindest thing anyone has done for him

 

Learn More

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.

Follow Patrick on Twitter at @patrick_oshag

Sep 1, 2020

My guest this week is Michael Mauboussin, the head of consilient research at Counterpoint Global. Michael is an all-time favorite guest here on the show, and this is his fourth appearance. We discuss one of the biggest topics in the world of investing: the shift from public to private markets that has taken place over the last several decades. We explore the reasons for this shift, the biggest overall changes in capital markets, and what the future may hold. Along the way we explore other fascinating topics like the rise of intangible asset investments, employee-based compensation as a form of financing, and more. If you enjoy this conversation I urge you to read Michael’s paper on the topic which will be linked in the shownotes. Please enjoy this conversation with Michael Mauboussin.

 

This episode of Invest Like The Best is sponsored by Canalyst. Canalyst is the leading destination for public company data and analysis. 

If you’re a professional equity investor and haven’t talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick.  

 

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.

Follow Patrick on Twitter at @patrick_oshag

 

Show Notes

(2:27) – (First question) – Motivation for writing the book from public to private equity

            (2:28) – Public to Private Equity in the US: A Long-Term Look

            (3:02) – The Incredible Shrinking Universe of Stocks

(4:48) – Size of the public vs private markets

(7:20) – History and changes in the public to private markets

(12:00) – Public market vs venture capital returns

(16:48) – Persistence of returns

(20:01) – Role of price and EBIDTA on the returns of a buyout

(23:31) – How buyout forms are sourcing the debt

(29:31) – Transition to businesses relying on intangibles

            (29:42) – Capitalism without Capital: The Rise of the Intangible Economy

            (30:13) – Endogenous Technological Change

            (30:36) – Should Intangible Investments Be Reported Separately or Commingled with Operating Expenses? New Evidence

            (34:18) – Explaining the Recent Failure of Value Investing

(36:21) – Superstar firms and increasing returns

(42:38) – Role on monopolies in creating network effects

(4:52) – The allocators perspective in these investments

(49:16) – How does this all impact public market active management

(51:54) – Advice to young people getting into the investment industry

            (52:30) – Jeremy Grantham Podcast Episode

(53:30) – Other areas he is researching/looking into

(55:44) – How investment work and Santa Fe research influence eachother

(56:54) – Investors to learn from

            (57:15) – John Collison Podcast Episode

 Learn More

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.

Follow Patrick on Twitter at @patrick_oshag

Aug 25, 2020

My guests this week are Jeremiah Lowin and Chetan Puttagunta. Jeremiah is the founder of Prefect.io, an open-source software company where my family and I are investors, and Chetan is a partner at Benchmark Capital. Both are past guests and good friends. I asked them on to help the audience understand the open source software business model. I’ve been fascinated with this model in which companies give a huge chunk of their work and value away for free to a community of developers, and then make money by building additional tools, functionality, and services on top of their free and open platform. While this may strike you as a wonky discussion on a niche software topic, I think it is valuable for everyone because the ideas can be applied to more than just code. I view much of my own activity as open-sourcing investment research and knowledge. It is also important because much of the world’s technology is built on top of open source projects. I hope you learn something new about this emerging category. Please enjoy.

 

This episode of Invest Like The Best is sponsored by Canalyst. Canalyst is the leading destination for public company data and analysis. 

If you’re a professional equity investor and haven’t talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick.  

 

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.

Follow Patrick on Twitter at @patrick_oshag

 

Show Notes

(2:40) – (First question) – Originator business in open source software; Redhat

(5:51) – Why open source is valuable in building a business

(7:40) – Examples of the benefits of open source projects

(10:27) – Open source business models that produce the best results

(17:04) – Defensibility of open source companies

(25:02) – Mentoring younger founders on using open-source

(30:54) – The benefits of launching open-source

(36:41) – Building a digital community

(41:31) – Lessons from Open Source that can be applied to other businesses

(50:04) – The opportunity sets available in the open source space

(53:33) – Future of open source

            (56:31) – Tobi Lutke Podcast Episode

 

Learn More

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.

Follow Patrick on Twitter at @patrick_oshag

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