Invest Like the Best with Patrick O'Shaughnessy

Latest Episodes:

Nick Kokonas - Know What You Are Selling – [Founder’s Field Guide, EP.8] Nov 19, 2020

Show notes

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.

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For more episodes go to InvestorFieldGuide.com/podcast.

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.

Follow Patrick on Twitter at @patrick_oshag

Niki Scevak - Wild Hearts and Wild Ideas - [Invest Like the Best, EP.200] Nov 17, 2020

Show notes

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.

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.

Follow Patrick on Twitter at @patrick_oshag

Todd McKinnon - Creating and Defining a New Market Category - [Founder’s Field Guide, EP.7] Nov 12, 2020

Show notes

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.

For more episodes go to InvestorFieldGuide.com/podcast.

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.

Follow Patrick on Twitter at @patrick_oshag

Jason Karp and Rohan Oza – The Power of Brand - [Invest Like the Best, EP.199] Nov 10, 2020

Show notes

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.

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For more episodes go to InvestorFieldGuide.com/podcast.

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.

Follow Patrick on Twitter at @patrick_oshag

John Chambers - Pattern Matching, Playbooks, and Winning Product Categories - [Founder’s Field Guide, EP.6] Nov 05, 2020

Show notes

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 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.

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.

Follow Patrick on Twitter at @patrick_oshag

Anu Hariharan – Lessons in Growth Investing - [Invest Like the Best, EP.198] Nov 03, 2020

Show notes

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

For more episodes go to InvestorFieldGuide.com/podcast.

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.

Follow Patrick on Twitter at @patrick_oshag

Laura Behrens Wu - When Digital and Physical Worlds Converge - [Founder’s Field Guide, EP.5] Oct 29, 2020

Show notes

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.

For more episodes go to InvestorFieldGuide.com/podcast.

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.

Follow Patrick on Twitter at @patrick_oshag

Brad Gerstner and Rich Barton – Thriving in Changing Markets - [Invest Like the Best, EP.197] Oct 27, 2020

Show notes

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

For more episodes go to InvestorFieldGuide.com/podcast.

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.

Follow Patrick on Twitter at @patrick_oshag

Jason Citron - Building the Third Place - [Founder’s Field Guide, EP.4] Oct 22, 2020

Show notes

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.

For more episodes go to InvestorFieldGuide.com/podcast.

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.

Follow Patrick on Twitter at @patrick_oshag

Ben Gilbert and David Rosenthal of Acquired - Lessons on Early Stage Investing and Getting Acquired - [Invest Like the Best, EP.196] Oct 20, 2020

Show notes

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

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

For more episodes go to InvestorFieldGuide.com/podcast.

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.

Follow Patrick on Twitter at @patrick_oshag

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