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Square One: Conversations with the Best in Business

Square One: Conversations with the Best in Business

By Romeen Sheth
Square One is a podcast where we interview founders, investors, and executives at the cutting edge of business. We discuss industry topics, careers and the journeys of how these individuals got to where they are today. We start at Square One.
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32: Brianne Kimmel, Managing Partner at Work Life Ventures

Square One: Conversations with the Best in Business

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95: Sid Viswanathan, Co-Founder & President of Truepill
This week we dove into healthcare. Everybody listening has had a subpar experience with our healthcare system - whether it’s a friend, a colleague, a family member or a personal experience, our healthcare system is fraught with challenges. Part of the reason the system is so difficult is because of how the incentives are set up - patients, primary care physicians, specialists, health care systems, insurance companies have a web of complex intertwined interests. That’s also what makes it so interesting to tackle. This week’s guest was Sid Viswanathan, Co-Founder and President of Truepill. Truepill has created an API to help enable pharmacy fulfillment and delivery, white label packaging and product design. Their goal - simply put - is to create a pharmacy infrastructure grounded in technology and automation to build a next generation healthcare platform. Sid and team have raised over $100M to bring this vision to reality. In this conversation we discussed the challenges of innovating in healthcare, how Truepill provides customers with a better experience and the ups and downs of leading a hyperscale business.
39:08
May 12, 2021
94: Manik Gupta, Former Chief Product Officer of Uber
One of the most transformational companies of the last 20 years has undoubtedly been Uber - in a sense it’s incredible to think in 15 short years we’ve come from the launch of the iPhone to now powering a global transport system with the click of a button on that same phone. This week I caught up with someone that was largely responsible for making that transformation a reality - Manik Gupta, Former Chief Product Officer of Uber. Manik and I spent time chatting about Uber, but also extended the conversation to leadership lessons and how he thinks about evaluating startups - we talked about how to think about resource allocation in hyperscale, the tradeoffs when developing product and the learning curve of leadership (he had over 1,000 people report to him in the span of 2 years). We rounded out the latter part of the discussion diving into an ecosystem both he and I have been actively investing in lately and are excited about - India.
46:59
May 11, 2021
93: Josh Clemente, Founder of Levels Health
We’re going through a renaissance period in consumer health right now - new tech enabled products are coming out for sleep, telehealth, diet, nutrition and more. This week’s guest took us deep into what optimizing the metabolic function looks like. As I learned in prep for this conversation, seven of the 10 leading causes of death in the U.S. are strongly related to metabolic dysfunction - metabolic function improves energy, endurance, memory, mood and cognitive performance. Josh Clemente has bought a biowearable metabolic sensor to market to help solve this problem - Levels is an innovative platform that pairs continuous glucose monitoring with an impressive software suite to provide the wearer with deep insights about their health. In advance of this conversation, Josh’s team sent my wife and I both a Levels to see how the product works and it was incredible - it provided us actionable health information and helped us understand how specific foods, exercise and timing of day affected our metabolic health. This episode was fun - Josh has experience at some of the most innovative companies in the world, like SpaceX and brought that experience to Levels to build a next generation category winner in healthcare.
57:40
May 4, 2021
92: Alex Bouaziz, Founder & CEO of Deel
We’ve talked a lot on this podcast about emerging and resulting trends that will stick with us a function of COVID-19: higher education being disrupted, consumer health being further tech enabled, the rise of crypto, and AI and machine learning impacting functionally every industry. But underneath the core of every industry we’ve talked about is people and global workforces. It’s why this week I was excited to chat with Alex Bouaziz, Founder and CEO of Deel. Deel is solving the incredibly complex and simultaneously important issue of global payroll. As workforces have gone remote and international over the course of the past year, Deel has developed software to help companies stay compliant with local laws and tax systems while keeping international onboarding smooth and seamless. Deel has raised over $200M over the past year and just publicly announced a $1B valuation.
38:16
May 4, 2021
91: Erik Torenberg, CEO of Village Global & Co-Founder of On Deck
Higher education is currently undergoing one of the most significant transformational shifts the world has ever seen. On this podcast, we’ve talked to a number of companies disrupting higher ed - online bootcamps, vertical labor marketplaces and coaching platforms. This week’s guest is taking aim at the entire "university bundle" - network, community, credentials and education. Erik Torenberg is the Founder and Chairman of OnDeck and CEO of Village Global, a $150M venture fund. On Deck aims to take the “university bundle” and apply it to the entire lifecycle of a person’s career. On Deck recently raised a $20M Series A led by Keith Rabois of Founder’s Fund to build “the Stanford of the Internet.” In this episode, Erik and I chatted about his early experiences at Rap.fm and being employee #1 at Product Hunt. We then dove deep into all things OnDeck - specifically, how he is thinking of building a new type of university that will be around for the next 100+ years.
41:16
April 28, 2021
90: Anthony Pompliano, CEO of POMP Investments
Crypto has taken the world by storm - a niche computer science topic less than a decade ago has finally entered the purview of mainstream today - Coinbase has filed to go public, institutions are accepting that Bitcoin and more broadly crypto should be a part of their asset allocation strategy and we’re starting to see a variety of interesting projects and applications take shape - one of the most popular as of late has been Bitclout. But it hasn’t always been so obvious or so popular. One of the earliest and most consistent proponents of bitcoin has been Anthony Pompliano, Co-Founder of Morgan Creek Digital and current CEO of Pomp Investments. In today’s conversation, Pomp and I discussed how his interest in bitcoin evolved - he was in the Army, led Growth teams at Facebook and eventually went full steam into crypto. We started at a foundational level breaking down questions like: “what is money” and evolved more deeply into BTC specifically and its implications. We spent the latter half of the discussion on Pomp’s budding media empire - with almost 700,000 followers on Twitter and a variety of other initiatives going, Pomp is building something special.
01:09:05
April 6, 2021
89: Li Jin, Founder of Atelier Ventures
Over the last few years, a new section of our economy has surged - what’s now known as the creator economy. Creators are individuals that are directly reaching consumers and participating and generating economic values through mechanisms previously unused. Now the idea of creating content online isn’t new, but what we’ve seen through trends over the last 5 years and a shock to the system in COVID has caused unparalleled momentum for the category. We’re now moving to a phase in this economy where it’s not just individuals sharing existing skills. Platforms are resegmenting and categorizing those skills in new ways - whether it’s NFTs or influencers - and in new business models. Li Jin is one of the most thoughtful individuals on what’s really going on in this space. Formerly a Consumer Investor at Andreessen Horowitz, Li has recently founded her own firm Atelier Ventures to specifically focus on the all the emerging activity in this space.
40:12
April 2, 2021
88: Tobenna Arodiogbu, Founder & CEO of Cloudtrucks
When you think of the most common job in the US - it’s pretty typical to think about service workers: retailers, cashiers, fast food. But the most common job in 29 states is truck driving. Over 3 million Americans work as truck drivers and hundreds of communities and over 7 million workers provide services to truck drives - including working at truck stops, loading and unloading freight and servicing vehicle. There’s been a lot of talk about the impact of self-driving technology and the implications for labor markets. One perspective is it’s going to take a lot of money off the table for truckers and we need to be resilient in the way we think through creating a transition pathway for many of those workers. The exciting thing is there’s a number of promising companies in the space that are working on providing more autonomy and tools to truckers to graduate up the stack - This week I chatted with Tobenna Arodiogbu - Founder and CEO of Cloudtrucks on exactly that topic. He’s raised over $25M and is focused on empowering truck drivers to leverage software to compete and participate in the new world order.
41:25
April 2, 2021
87: David Sacks, Founder of Craft Ventures
There are few individuals in the world that have seen, built and led multiple of the world’s iconic companies. David is one of them. He was a core member of PayPal and served as the company’s first product leader and COO. David went on to found enterprise collaboration company Yammer, one of the fastest growing SaaS statups in history - Microsoft acquired Yammer for $1.2B just 4 years after its founding. Not only has David been a successful founder, but he has also been one of the most impressive investors in tech, having personally invested in over 20 unicorns, including Affirm, AirBnb, Facebook, Lyft, Opendoor, Palantir, Postmastes, Reddit, Slack, SpaceX, Twitter and Uber amongst others. I got David’s thoughts on a variety of lessons leading, operating and investing in multiple multi-billion dollar companies.
41:13
March 18, 2021
86: Michia Rohrssen, Founder & CEO of Prodigy
The classic American dream consisted of three things: (1) a suburban house, (2) a pension and (3) a car. The Internet era transformed each of those elements - people became more attracted to cities as our economy became services oriented, companies shifted to the 401k and other retirement products and our usage of cars has transformed with Uber and Lyft. But while the experience of cars has changed, purchasing cars has largely stayed the same.You go to a dealership, look at all the cars, find one you like, test drive it, haggle over the price and then drive home. It’s a transaction almost everyone goes through. It’s why I was excited to chat with Michia Rohrrsen, Founder & CEO of Prodigy this week. Prodigy has reimagined the car buying experience and expanded the possibilities of automotive retail when software is introduced every step of the way. We talked about the digitization of car buying and what the ideal dealership would look like.
49:05
March 10, 2021
85: Jeremy Cai, Founder & CEO of Italic
This week we went deep into e-commerce. E-comm has been all the rage throughout COVID and it makes sense why: we’re all at home now and brands are able to get to us in more and more ways. A company I’ve been keeping an eye on in the e-comm space is Italic, a marketplace for luxury goods; in this episode I chatted with Italic’s Founder/CEO Jeremy Cai. Lux goods are interesting - they’re desired but super expensive. What I didn’t know originally was how much of that money is kept by the brand vs. the actual manufacturer. Italic has flipped the model and unlocked manufacturers ability to sell directly to consumers. So now you can buy products from the factories that make Prada, Gucci, Tumi, etc. at factory price. A win for the manufacturer and a win for the consumer. Jeremy walked me through the way he thinks about e-comm, what the US can learn from China, where the value is trapped in this space and how to build a world class consumer experience.
48:43
March 8, 2021
84: Andrew Yang, Candidate for Mayor of New York City
Over the past 3 years, it's been a great honor of mine to develop a friendship with Andrew Yang. I remember walking down a street in New York City a few years ago with Andrew talking about all the challenges we faced as a society - he looked at me with determination and said: if we want to solve the problem, we need to be a part of the solution. Since deciding to run for President, Andrew raised the level of discourse in our country and forced us as a citizenry to challenge many of our most basic assumptions. He has elevated a vision for a more humane capitalism and stressed the importance of country allegiance over party allegiance. Andrew had a sentiment he often used to express on the campaign trail - his vision and policies were not about moving the country left or right; rather, they were about moving the country forward. Andrew joined me and 30 of Atlanta's most senior leaders for an intimate fireside chat to provide a perspective on how we move forward as a society. Since then he has announced his candidacy for Mayor of NYC and I'm thrilled to be an early and avid supporter. Enjoy the fireside chat. 
43:53
February 23, 2021
83: Chris Bakke, Founder and CEO of Laskie
Professional services is simultaneously one of most difficult and attractive opportunities to disrupt today. On one end of the spectrum you have large consulting firms like McKinsey and on the opposite side you have freelance platforms like Upwork. But the middle hasn’t really been fulfilled. And with more companies in the middle being startups/technology businesses, the void has never been larger. So this week I chatted with Chris Bakke, Founder and CEO of Laskie on how he’s thinking through the future of professional services. Chris sold his previous company to Indeed and was Head of Product where he led a suite of products that helped 250M+ find their next job. In this conversation Chris and I unpacked the professional services landscape, specific opportunities that can create the highest impact and some of the misnomers/myths of this market.
52:26
February 23, 2021
82: Tim Ellis, Founder and CEO of Relativity Space
On this podcast we frequently chat with Founders changing the world - everything from autonomous checkout to vertical labor marketplaces to the creator economy and the no code movement. But one of the areas I’ve been most recently intrigued by is space. And so this week we talked to one of the sharpest and most interesting entrepreneurs in today’s space movement - Tim Ellis, Founder & CEO of Relativity Space. Relativity’s mission is to make mankind a multi-planetary species. To make this mission a reality, the company is radically changing the infrastructure and manufacturing process to build a rocket shrinking the launch process from 180 months to 60 days. How they’re doing this is what’s especially mind blowing to me - 3D printing. In this episode we talked about the space economy, 3D printing, aerospace supply chains and how Tim is using a fresh fundraising round of $500M to change the way we think about space.
47:47
February 18, 2021
81: Julien Smith, Founder and CEO of Practice
Coaching and mentorship is one of the simultaneously overrated and underrated topics. It’s overrated because we talk about it a lot and recognize the importance of coaching, but it’s underrated because we have a perception that there’s a fixed barrier to be a coach and there’s a finite number of coaches in the world. But what if you could leverage technology to abstract away all the difficult parts of running a coaching practice and give coaches a platform where they could focus on their true strengths. The result would be significant market expansion and additional coaches being unleashed into the world. This has interesting at scale ramifications - we could move to a world in which everyone in some sense has a personal coach, unleashing our own personal creativity by an additional factor. These possibilities are what we talked about this week with Julien Smith, Founder and CEO of Practice. Julien was formerly the Founder/CEO of Breather, where he raised over $120M to revolutionize co-working spaces. Julien is one of the most interesting entrepreneurs of our generation and I had to bring him back after we had a great discussion in Episode 41. In this conversation we touched on scaling, self awareness, behavior change, pricing power, and support networks.
36:39
February 16, 2021
80: Hiten Shah, CEO of FYI and Former CEO Kissmetrics
How would you feel if you had a billion dollar opportunity right in front of you and you squandered it? That’s what we talked about this week with Hiten Shah, CEO of FYI and former CEO of Kissmetrics. Hiten coined the term “my billion dollar mistake” in an iconic blog post several years ago. In it, he detailed how his team at Kissmetrics was 3 years ahead of the market, well funded, had great customers and ultimately lost the lead. It was a lesson in management, leadership and self awareness. This week I chatted with Hiten about all things leadership and management - we dug deep specifically into lessons learned from that experience, but also broadened it out to his observations of what’s going on in the market today - how are Founders in 2021 approaching fundraising, what are the common mistakes they’re making and what, if any, downstream impacts will the abundance of capital have on the early stage ecosystem.
57:37
February 2, 2021
79: Jonathan Hsu, Co-Founder of Tribe Capital
This week we went deep on the impact of data science in venture capital. Most investors form their experience based on a combination of anecdote, pattern recognition and experience. And candidly over the majority of time venture capital has been a meaningful asset class, there hasn’t been another way to do it. The last decade has fundamentally changed that - as compute power has significantly increased, the ability to store, harness and analyze data has transformed. Not only has this led to many of the most prominent businesses of our time - e.g. companies likes Facebook and Slack - but it’s also fundamentally opened up a new approach to investing. I chatted with Jonathan to dissect this phenomena. Tribe has pioneered one of the most novel frameworks in the industry - akin to traditional accounting and financial statements - to unpack early stage technology businesses. We touched on a number of topics: (1) the myth that product market fit can’t be quantified, (2) the 3 fundamental units of analysis that every early stage company can be dissected against and (3) finding atomic units of value in businesses.
35:49
January 29, 2021
78: Avlok Kohli, CEO of AngelList Venture
This week we dove into the future of venture capital. For an industry that is singularly focused on disruptive innovation, venture capital has largely stayed out of the spotlight from new challengers and disruptors. Until now. It’s why I was so excited to chat this week with Avlok Kohli, CEO at AngelList Venture on the future of venture capital, opportunities for innovation in the system and the implications for expanding entrepreneurship. AngelList Venture is focused on answering the question - what is possible if software played a bigger role in how we financed companies. Avlok brought a deep first principles perspective to the show and we touched on a number of topics: (1) the importance of expanding the pie vs. zero sum thinking, (2) how a venture fund would be built today if it was on the rails of software vs. traditional service guilds, (3) how the internet gives creators infinite leverage and (4) why we are in the bottom of the first inning for technology.
48:40
January 21, 2021
77: Nick Donahue, Founder and CEO of Atmos
This week we’re diving into the future of homes. The 3 henchmen of the American economy are education, healthcare and construction. Construction and real estate have always been a pretty underrated topic in tech - but it’s one of the markets that has an almost limitless TAM. The global stock of institutional grade real estate is set to triple over the next 15 years with some estimates pegging aggregate values at ~$70 trillion. It was a pleasure to have Nick Donahue, Founder and CEO of Atmos on the show today. Atmos is creating a full end to end solution for consumers to build custom homes. I love what Nick and team are building and I invested in him after he came out of YCombinator. In this conversation we touched on a number of topics: (1) COVID’s affect on national real estate prices, (2) how software allows you to vertically integrate in construction, (3) building a business that deals with atoms, not just bits and (4) dismantling the myth that you need to be a homebuilder to provide consumers a 10x experience when purchasing homes.
24:31
January 12, 2021
76: Jason Traff, Founder and President of Shipwell
This week we went deep on supply chain and logistics. I know what you’re thinking - supply chain isn’t exactly the sexiest topic, but it’s deceptively important. Every commerce transaction in the world requires interdependent supply chains. There are very few businesses where it feels like the proxy for the market size is some variant of GDP. Amazon is a really obvious example of a business that would fit this description. Shipwell is another. It’s why I was so excited to speak with Jason Traff, Founder and President of Shipwell this week. Shipwell has raised over $50M to develop a supply chain operating system for the enterprise, transforming supply chains by replacing manual process with a fully connected logistics ecosystem. Jason and I talked about a lot of topics in this conversation - (1) the fundamental leaps in quantum computing that power a company like Shipwell to exist, (2) how big of an opportunity this really is, and (3) how he’s grown 400% through COVID.
42:20
December 10, 2020
75: Nikhil Basu Trivedi, Former General Partner at Shasta Ventures
This week we dove deep on what in the world is going on in venture capital - we started off in March with a Black Swan Memo from Sequoia on how COVID was going to fundamentally disrupt the economy. There’s no question that happened, but what’s happened for startups and technology hasn’t been as intuitive - the capital markets are more active then ever, technology businesses are booming and deals are getting done at breakneck speed. This week I chatted with Nikhil Basu Trivedi, Former GP at Shasta Ventures to unpack what’s going on. Nikhil coined the term “solo capitalist” this year and it speaks to a really interesting dynamic in the venture landscape. In this conversation we talked about: (1) agglomerators vs. specialists and how to chart positioning of different firms in the ecosystem, (2) price elasticity on venture deals and why different firms’ have different sensitivity thresholds when pricing deals, (3) what matters the most in a fundraise, (4) and the rise of solo capitalists.
38:46
December 3, 2020
74: Josh Childress, CEO of Landspire Group and Former NBA Player
“More than an athlete” is a phrase that’s significantly taken off over the past year. But it’s not just a phrase - it’s lifestyle, sentiment and mindset. That’s why I was so excited to have Josh Childress, CEO of the Landspire Group and former NBA Lottery Pick on the podcast this week. Josh is the perfect embodiment of the American dream. He grew up in inner city Compton, went to Stanford, had a successful NBA career and has transitioned to a successful real estate investor having an impact on local communities across the country. We talked a lot about mindset and being bigger than yourself in this episode. We talked about the psychology of putting your best foot forward and honing in on a larger purpose. Josh has worked tirelessly to create opportunity for minorities in the country and in many ways is just getting started on the impact he will continue to have for years to come. Some of my favorite topics we discussed in the conversation were: (1) his background growing up in Compton, (2) his experience in the NBA and playing overseas, (3) the misconceptions of mental health for athletes, (4) his entry into business via owning a laundromat and (5) why he always pushes himself to be the least smart person in the room.
01:05:28
November 17, 2020
73: Sahil Lavingia, Founder and CEO of Gumroad
This week it was awesome to dive deep into startups with Sahil Lavingia, Founder and CEO of Gumroad. Sahil’s seen it all in Silicon Valley - he was employee #2 at Pinterest, started Gumroad with a traditional venture backed structure, pivoted the business to be venture free and now has a rolling fund he operates in his spare time investing $7M a year in startups. We talked a lot about the differences in running a venture backed company vs. a company that lives and breathes off the balance sheet. We chatted about the difference in psychology of running these types of businesses and how clarity of thought comes through when you get out of the echo chamber. Sahil has worked to remove friction and increase democratization in nearly everything he’s done - a lot of this principle is what underscores Gumroad. He’s taken this same perspective to investing. Some of my favorite insights from this conversation include: (1) how to leverage community and audience, (2) why everyone should invest in early stage companies, (3) the trope of the world’s venture capital being perfectly allocated and (4) how democratization and access will continue to lift humanity out of its early J curve.
50:58
November 11, 2020
72: Tom Uebel, Co-Founder and CEO, CommandE
Whenever I watch engineers work, it feels like an alternative universe. Not least of which is because devs have unique superpower tools at their disposal - tons of different productivity hacks and niche plugins; one of the things I've been interested in most lately is finding overlapping use cases between technical and non-technical folks and then diving into the use cases where there are tools for technical folks, but nothing for non-technical folks. That's how I found the guys at CommandE. CommandE has developed the ultimate cross-app search tool. I chatted with Tom Uebel, Co-Founder and CEO on how he came up with the idea, what the product looks like today, how he sticks out in a crowded space and developing implicit virality. Tom has raised from great folks like First Round, Bain Capital and Craft Ventures - this episode was fun diving into how he believes the future of search will unfold.
33:32
October 21, 2020
71: Shaan Puri, Former CEO of Bebo and Host of My First Million Podcast
This week we're talking concepts! It was awesome having Shaan Puri, Former CEO of Bebo on the podcast to chat through a number of them. Shaan and I go way back - we went to Duke together; since then we've formed a tight knit friendship as we've both gone through a number of different startup experiences as investors and operators. After selling his latest company to Twitch, Shaan set out on a host of projects: a podcast that has 2M+ downloads, a $3M rolling fund to invest in startups, an online course and a few other ventures.  In this conversation, we dug into a bunch of concepts and frameworks both Shaan and I have learned over the years. A few of my favorites included: (1) how to pack 4 years of experience in 1, (2) knowing when to shut a project down, (3) the challenges in a business as a function of the CEO's psychology, (4) a 5 part framework for change, (5) how to get "unstuck" and (6) a 2x2 for startup ideas. This one was a blast; Shaan's an idea machine.  Visit his personal site at www.shaanpuri.com to learn more about his projects / ventures. 
47:44
October 15, 2020
70: Saahil Goel, Founder and CEO of Shiprocket
This week it was awesome to dive deep into the future of e-commerce and shipping in India with Saahil Goel, Founder and CEO of Shiprocket. Shiprocket is the fastest growing e-commerce solution in India today; COVID has accelerated the business significantly and Shiprocket is shipping over 3 million packages a month now. This conversation was particularly interesting because it was targeted on the Indian market - a low trust consumer economy filled with micro transactions fulfilled by cash. Saahil gave a thoughtful perspective on how to increase transaction trust and why bringing transparency to checkout is the key unlock for mom and pop businesses in India. We touched on a number of interesting concepts: (1) first and foremost - the steps of an e-commerce transaction, (2) focusing on trust in the transaction, (3) building out an ecosystem of partners / integrations and taking a Shopify approach, (4) why post checkout is where loyalty begins for SMBs and (5) building a hyper growth company in India.
51:56
October 1, 2020
69: Michael Mayer, Founder and CEO of Bottomless
This week it was awesome to dive deep into the future of e-commerce with Michael Mayer, Founder and CEO of Bottomless. Bottomless is an intelligent subscription - instead of getting shipments on a set schedule, you get shipments based on usage. This is a fundamental unlock/new insight: Michael believes that our current e-commerce infrastructure models Internet 1.0. Bottomless is the next wave of how we take offline information, online into an organized intelligent schema and subsequently use information technology to move up the s-curve of innovation in this space. In this conversation we dove into a bunch of interesting concepts: (1) why 50% of a company is baked in from the founding moment, (2) how information consumption and focused dissatisfaction is the recipe for original insights, (3) why the unlock in grocery 2.0 is solving an information problem, (4) the characteristics of products that are good candidates for automatic reordering and the byproducts for privacy when a company like Bottomless succeeds at scale.
51:58
September 24, 2020
68: Ruben Harris, Co-Founder and CEO of Career Karma
Since the pandemic, over 100,000 students have skipped filling out financial aid and lower cost local institutions are seeing significant enrollment decline. This is exactly why we need 2.0 institutions that are working towards incentive alignment in education. This week, I dove deep into this topic with Ruben Harris, Founder and CEO of Career Karma. Career Karma simply put is Tripadvisor for your career - it's a managed marketplace focused on connecting high potential individuals with the right skills accelerators to help them harness their potential. In this conversation we talked about a number of topics: (1) unbundling higher education, (2) why Ruben is bearish on resumes and credentialing, (3) how the job market today mirrors the free agency process in sports, (4) how to unlock organic distribution - CK pumps over 700 pieces of unique content in addition to user generated content every month, (5) his early DMs with Balaji Srinivasan (former CTO, Coinbase) on how to break into tech / ultimately building a product for himself and (6) the recent Harvard Business School Case Study on CK.  We rounded out the conversation with Ruben's entrepreneurship motto and what drives him to build CK. 
58:15
September 17, 2020
67: Kat Cole, COO and President of FOCUS Brands
This week it was a pleasure to have one of the best and most thoughtful operators in the country join us - Kat Cole, COO and President of North America for Focus Brands. Focus Brands - while unknown to many consumers as a parent company - owns companies that are mainstay language in most American households - Cinnabon, Auntie Anne's, Moe's, Jamba Juice and more. In this conversation we explored two big themes: operating and brand building. We spent the first half unpacking operating principles: (1) how to change mindsets, (2) how to evaluate compelling opportunities, (3) solving for being right vs. being curious, (4) curiosity and humility as the foundation for courage and confidence, (5) possibility vs. positivity filters and unpacked each through examples. In the second half we dove into all things brand - namely, how to build, differentiate and sustain brand. We rounded out the conversation with Kat’s sources of learning and ground truth motto she lives by. This was one of the most knowledge packed conversations we have had and it was fun to have Kat on the show.
51:58
September 9, 2020
66: Jacob Helberg, Senior Advisor - Stanford University Cyber Policy Center
Over the last 6 months, without question, one of the most nuanced geopolitical relationships has made it to the forefront of mainstream media. This week we answer the question - what in the world is going on with the US and China. The tech community has taken a very strong perspective on US-China relations and there are a number of complex intertwined issues to unpack. Jacob Helberg is one of the most respected and thoughtful policy experts on this topic. Jacob currently serves as a Senior Advisor at the Stanford University Cyber Policy Center and is an Adjunct Fellow at the Center for Strategic and International Studies (CSIS) where he is writing a forthcoming book on U.S. foreign policy and national security, technology policy and China. Previously Jacob served as a Senior Policy Advisor at Google.  In this conversation we unpacked: (1) whether the US and China are in a Cold War, (2) the TikTok Ban and implications for future Executive Orders, (3) whether US-China relations are fracturing the global internet and (4) the plausibility of re-shoring supply chains.
43:28
September 1, 2020
65: Turner Novak, General Partner at Gelt VC
Tik Tok is one of the most phenomenal consumer stories of all time. Seemingly coming out of nowhere, Tik Tok has made an absolute splash in US culture over the past year. But the start of TikTok has a more deep rooted story in the way consumer social products have been evolving over the past decade. In this conversation, I chatted with Turner Novak, General Partner at Gelt VC on all things consumer social. Turner is one of my favorite sources of knowledge on what’s going on in consumer today - he has a deep perspective on international social products and how they translate in the US. In this conversation, we dove deep into the history of consumer social, how TikTok differentiates from other products from a front and back end perspective, what he thinks about Facebook Reels, the impending/potential TikTok-MSFT merger and what are future business models that are byproducts of social he’s excited to see.
59:35
August 18, 2020
64: Laura Behrens Wu, Founder and CEO of Shippo
Since the start of COVID-19, we have made unprecedented advances in e-commerce. Coined the “great retail acceleration”, US E-Commerce Penetration (as a % of retail sales) grew from 5.5% to 16% from 2009 to 2019. Within 8 weeks post Apr 2020, it grew from 16% to 27%. We have experienced 10 years of e-commerce growth in the last 8 weeks alone. When we think of e-commerce, we often talk about the frontend; both Shopify and Amazon are public tech darlings in the market right now and with good reason. But what we often don’t talk about is the unsexy backend - delivery of e-commerce. It’s why I was so excited to chat with Laura Behrens Wu, Founder and CEO of Shippo. Simply put, Shippo has created the best multicarrier software layer for e-commerce businesses to help streamline the fulfillment process. Laura has raised $60M+ from some of the best investors in the world on the backs of continual explosive growth pre-COVID and post-COVID. We touched on a number of topics in this discussion and Laura intricately explained the nuances of how to think about shipping in a time of explosive growth and operationally how she is leading her business during COVID.
43:27
August 5, 2020
63: Alex MacCaw, Founder and CEO of Clearbit
Management principles are some of the easiest topics to discuss, but some of the most challenging to put into practice. The best managers and leaders have an art in making problems so interesting and their solutions so constructive, that everyone wants to get to work and deal with them. This week I was excited to have one of tech’s best thinkers on management principles come on the show. Alex MacCaw, CEO of Clearbit, has recently put out a book titled The Manager’s Handbook - in it he takes his experience as one of the first employees at Twitter, first 20 at Stripe and now leading Clearbit - a company that has raised ~$20M - and translating it to distinct principles and tactics. We discussed a host of concepts in this discussion: (1) how to manage yourself, (2) personal systems of action, (3) failure points, (4) ICs vs. managers, (5) mental and physical health, and (6) leading through COVID. Here’s the link to Manager’s Handbook: https://themanagershandbook.com/?ref=producthunt
50:30
July 29, 2020
62: Mallun Yen, Founder and GP of Operator Collective
The Founders we have had on the show have collectively raised over $1B in venture capital. I’ve heard which investors they enjoy working with, which are most helpful, which are not so helpful but the consistent piece of feedback I have heard is the desire for a more diverse cap table and a more operator centric focus. It’s why I was so excited to chat with Mallun Yen, Founder and GP of Operator Collective this week. Operator Collective was founded on the belief that venture capital concentrated among a homogenous group doesn’t represent where the tech industry is now or where it’s going. Operator Collective has created a new access point for operators from diverse backgrounds; the $50M fund has over 100 LPs, of which 90% are women and 40% are POC. The LP base is filled with many of the best operators in the world having representation from the C-suites of tech’s fastest growth businesses (Stripe, Zoom, Pagerduty, TaskRabbit, Salesforce and more). It was so fun to chat with Mallun. She truly opened my eyes with her thoughtfulness. Around the 50 min mark, after we ended the official podcast, Mallun and I continued the conversation for a few hours. Neither of us knew it was recorded, but I’m so glad it was - we decided to share excerpts from our conversation to continue to add perspective to how we can drive for a more inclusive tech industry. This was one of my favorite episodes I’ve done to date.
01:35:47
July 21, 2020
61: Ryan Delk, Founder and CEO of Primer
This week we dug into the future of education, but a bit differently than in ways we’ve previously explored - we talked homeschooling. COVID-19 has placed 74 million children in the US in some version of homeschooling overnight. Innovation in education is a massive opportunity. Thriving in a complex world requires creativity and original thinking, but our education system is designed for mass production — not unlocking imagination and individuality. We won’t be able to solve 2050s challenges with an educational supply chain built for the 1950s. Now is the time to dig into homeschool from first principles. It’s why I was so excited to chat with Ryan Delk, Founder and CEO of Primer. Simply put, Primer is homeschool with superpowers. As Ryan described to me in our conversation, the education system is systematically underestimating our next generation; Primer is building a learning experience well suited for 2020. We dug into a number of topics in this conversation: (1) the growth of homeschooling, (2) distance learning vs. homeschooling pedagogy, (3) the benefits of unencumbered creative time, (4) why homeschooling gets a bad reputation and (5) how teachers are the current heroes of our time.
45:33
July 14, 2020
60: Immad Akhund, Founder and CEO Mercury Bank
This week we dug into the future of banking. When you think of the macroeconomy top down - banking and financial services are bar none the largest market in the world, constituting just around ~20% of GDP. Even though the market is so large, we’ve continued to see consolidation and asset aggregation in the largest institutions in the world - and for historically good reason: banking requires strong compliance, risk and trust protocol. After we hit the onset of the financial crisis, trust began to erode in many large financial institutions and we started to see the onset of the challenger bank. Banks focused on a targeted experience and technology set attractive for millennial and Gen Z consumers. This week I chatted with Immad Akhund, Founder and CEO of Mercury Bank. Simply put, Mercury is a bank for startups. In this conversation we talked about the evolution of the banking experience, the landscape of consumer banking, how he thinks about every company seemingly becoming a fintech bank these days and leading a company in the time of COVID.
39:08
July 8, 2020
59: Keith and Gelena Wasserman (CEOs of Gelt and Skya Ventures)
This week we dug into real estate - when I had JD Ross, Co-Founder of Opendoor on the podcast, we chatted about how massive of an opportunity real estate is - the global stock of institutional grade real estate is set to triple over the next 15 years with some estimates pegging values at $70 trillion. It’s why I was so excited this week to chat with Keith and Gelena Wasserman (CEOs of Gelt and Skya Ventures respectively). Keith and Gelena started in this industry from scratch at the peak of the recession in 2008. Fast forward a little over 10 years and they’ve amassed a portfolio with an asset value of over $1.3B. In this episode we explored a couple different themes. We talked about the nuances of real estate - the fundamentals, how to value a property, characteristics of a good investment; we talked mentality (an immigrant’s mindset, an entrepreneur’s mindset and the philosophy of “making money on the buy). And we snuck in a little bit of tech - impact of tech on real estate, cloud kitchens and autonomous vehicles and the early stage venture fund Keith and Gelena started to get exposure to other industries.
55:17
June 23, 2020
58: Matt Mazzeo, General Partner at Coatue
It’s been well documented that Hollywood and Silicon Valley have always had a close relationship - even though these industry centers exist within the same state, the underlying state of mind has always been somewhat different. There is a clear perspective to be had with melding the best of both worlds. This week’s guest has been at the forefront of that intersection. Matt Mazzeo spent his formative years at CAA, joined Chris Sacca as Managing Partner of Lowercase Capital and is now a General Partner at Coatue Management. Matt is one of the sharpest consumer investors in the world and we touched on a number of topics including: (1) the blending of the Hollywood/Silicon Valley mindset, (2) his partnership and time at Lowercase, (3) how he’s thinking about a post COVID world and (4) the future of education and rehiring.
50:58
June 17, 2020
57: Sean Linehan, Co-Founder and CEO Placement
In the last several months, I’ve had a number of Founders on the podcast building companies to drive innovation in how we work. A timely issue given pre-COVID 19, one in four Americans lived in locations with little or no economic growth; meanwhile tens of millions of city dwellers are increasingly squeezed by rising costs of living. This has only been exacerbated by COVID-19. I was excited to chat with Sean Linehan, Co-Founder and CEO of Placement this week to further that dialogue. Placement’s mission is to unlock the earning potential of millions of Americans. Placement is the modern day talent agent - enabling individuals to land opportunities in fast-growing, affordable cities or in remote roles. By reducing friction and eliminating the barriers to geographic mobility, Placement is shifting who captures the value in the country’s economic growth. We touched on a number of topics in this episode: (1) location arbitrage, (2) flipping the funnel, (3) what at scale data tells us about economic mobility, (4) democratizing access and process to landing higher paying jobs, (5) engineering momentum and (6) the decision to focus solely on placement (vs. admissions and training).
52:32
June 11, 2020
E56: Daniel Gross, Founder and CEO of Pioneer
Daniel Gross is one of the most interesting members of the startup community today; he is the youngest YC founder in history and sold a company to Apple at 23 where he ultimately rose to lead Apple's efforts in machine learning. After his time at Apple he joined YC as a Partner in 2017 and ultimately moved on to found Pioneer. Pioneer is a fully remote accelerator dedicated to funding projects and startups built by the ambitious outsiders of the world. Daniel founded Pioneer to provide some of the non-intuitive benefits of Silicon Valley to many more people. Pioneer provides capital to jumpstart ideas, but most importantly Pioneer broadens people’s horizons of how they view themselves. We spent this conversation talking about a number of topics: (1) how the world will bounce back from COVID, (2) the philosophical underpinnings of Pioneer (e.g. believe in oneself, curiosity, etc.); (3) the nature of games and (4) why an organization like Pioneer is so valuable to flattening the innovation curve.
44:11
June 2, 2020
55: Arjun Sethi, Co-Founder and Managing Partner, Tribe Capital
Tribe Capital is one of the most interesting firms in all of venture capital today - a highly quantitatively driven firm, the Tribe team comes from deep data science backgrounds at leading companies like Uber and Facebook and applies an operator's lens to investing. I was excited to chat with Arjun Sethi, Co-Founder and Managing Partner at Tribe this week. We touched on a number of topics: (1) the transition from operator to investor, (2) the lingua franca of 2020 businesses, (3) quantifiable frameworks (e.g. how to quantify product market fit), (4) underwriting risk and capital allocation across stages, (5) loss ratios, (6) force multipliers, (7) atomic units of value, (8) 1 of n vs. n of 1 companies and (9) retesting underlying assumptions in the era of COVID-19. This was one of the longest discussions I've had on the podcast and one of the most interesting. Arjun is a wealth of knowledge. 
01:31:30
May 27, 2020
54: Rebecca Kaden, General Partner at Union Square Ventures
Union Square Ventures is one of the most revered venture firms in New York City. This week I was thrilled to chat with Rebecca Kaden, General Partner at USV. We started off the conversation talking about some of Rebecca’s fundamental beliefs on how to succeed in venture - primarily the importance of matching horizontal and vertical perspective and providing value in each interaction. We then spent the majority of the dialogue on USV’s Thesis 3.0 and dove deeply into the future of education before rounding out with how Rebecca expects venture capital to change over the coming years.
34:55
May 27, 2020
53: Allison Barr Allen, Co-Founder and COO of Fast
Checkout is one of the oldest and most painful elements of a purchase process. If you're buying something other than on Amazon, chances are you have to re-login. There is a significant conversion dropoff for businesses when this happens and a subpar experience for consumers. Fast is here to fix that. Fast wants to be the intermediary for consumer interaction - in simple terms, Fast wants to provide consumers with a one-click login, one-click payment and one-click data collection.   This week I chatted with Allison Barr Allen, Co-Founder and COO of Fast. Fast raised $3M last November and followed up with an aggressive $20M raise just 4 months later. And for good reason. Today Fast's product is login, but at scale Fast could solve the problem of silo'd identity on the internet and be the central repository for all identity management. This conversation was a ton of fun and I learned a lot from Allison. 
32:46
May 13, 2020
52: Mike Slagh, Founder and CEO of Shift
More than 25 million Americans were laid off in April and that’s just the official count. Economists are estimating that unemployment could soon exceed 30% and have massive sectoral impact - service and retail to engineering and product management. Traditional tools - job boards, LinkedIn, etc. are going to be challenged at handling the volume we will be seeing over the next few years - this is where vertical labor marketplaces come in. This week I was thrilled to chat with Mike Slagh, Founder and CEO of Shift. Shift is a digital talent marketplace and community that connects veterans with world class companies. Shift aims to map military backgrounds to specific hiring needs while helping veterans acquire new skills, secure referrals and master corporate hiring processes. Shift extends full stack from education and re-skilling to mentorship and coaching.
30:25
May 11, 2020
51: Allison Robinson, Founder and CEO of The Mom Project
There’s a fundamental problem in the workforce today - 43% of skilled women exit the workforce after having children. The economic loss we face from this input is dramatic. We know anecdotally and scientifically that gender diversity (amongst other forms of diversity) materially improves the bottom line. Though that may be the case, we’re not doing a great job to re-engage this workforce. This is why this week’s guest - Allison Robinson - built The Mom Project. The Mom Project is a digital talent marketplace and community that connects professionally accomplished women with world class companies. I think of The Mom Project as the best of a staffing company, best of a job board, wrapped in a differentiated community, all empowered by best in class technology. Allison has raised $10M+ from some of the best investors in the world, has Serena Williams as a key advisor and is facilitating opportunity for over 250,000 moms on her platform today.
39:23
April 20, 2020
50: Jason Boehmig, Founder and CEO of Ironclad
There's one document that every business lives on - contracts. But the contract management space and legal industry more broadly has been a historical laggard of innovation and technology adoption. Enter Ironclad. Ironclad simply put is a startup that makes it easier for legal teams to manage their contract workflow. This isn't a small problem by any stretch - the company has raised over $80M from Sequoia, Accel, Emergence Capital and Y-Combinator Continuity to fundamentally change the interaction model between businesses and their contracts. I chatted with Jason Boehmig, Founder and CEO at Ironclad on how he's building one of the most interesting companies in the legal industry today. 
28:25
April 16, 2020
49: Des Traynor, Co-Founder and Chief Strategy Officer of Intercom
All disruptive technologies start selling first to early adopters in the market. As the customer base and market matures, successful disruptive technologies evolve adding sophistication that larger customers need at scale. Intercom is a perfect example of this - first selling to companies in their Y-Combinator batch, today Intercom has raised over $250M and counts over 30,000 organizations as customers. Intercom is one of the fastest growing SaaS startups of all time and with good reason - the team had a fundamental perspective on how to make a Messenger product for the enterprise and has translated this vision into a robust and holistic customer communication platform that services the full lifecycle for internet businesses - from acquisition to engagement and engagement to retention. I chatted with Des Traynor, Co-Founder and Chief Strategy Officer at Intercom on all things Intercom and leading a high growth startup.
56:57
April 12, 2020
48: Steven Galanis, Founder and CEO of Cameo
Historically access to celebrities was far removed and impersonal - glossy center magazines and billboards, fans were unable to interact with their favorite stars. Social media has fundamentally changed the interaction model; talent has increased its ability to leverage fandom into commercial opportunity and fans have come to expect more and more personalization and engagement. Cameo has fundamentally changed the game. Started just 3 years ago, the company has raised $56M to facilitate personalized messages from celebrities to fans. In this episode, I chatted with Steven Galanis Founder and CEO of Cameo and we touched on a number of topics including: (1) how the internet has changed engagement, (2) the network effects of building a fast growing marketplace business, (3) why Cameo is best positioned to compete against Instagram, Snapchat and YouTube, (4) the responsibilities that come with a fast growing, B2C organization and (5) ancillary use cases that can be created of Cameo at scale.
42:32
April 7, 2020
47: Hunter Walk, Co-Founder and Managing Partner Homebrew Ventures
This week's episode took a different turn than our normal programming. COVID-19 has ravaged every sector of the economy; while BigTech has stayed relatively flat and certain areas have seen unprecedented demand, the vast majority of the world is working through an excruciatingly tough,  once-in-a-century type event. This week I chatted with Hunter Walk, Co-Founder and Managing Partner at Homebrew Ventures. Hunter and team have $200M in assets under management and have invested in some of the biggest generational winners of our time including Plaid, Bowery Farming, Chime, BuildingConnected and Cruise amongst others.  We talked all things tech and venture capital during this incredibly trying time. 
57:05
April 2, 2020
46: Jordan Fisher, CEO Standard Cognition
Autonomous vehicles have been all the buzz over the last few years. Not to be outdone, Amazon has quietly been applying this same technology to checkout. In 2018, Amazon announced "Go" - a grocery story with frictionless checkout. Since then, Amazon has been building and launching stores across the country. While promising from a technology perspective, retailers have fears of being locked in the Amazon ecosystem; we saw the same net effect play out with Instacart. As Amazon acquired Whole Foods retailers turned to Instacart to offset Amazon's delivery capability.  Enter Standard Cognition (SC). SC is building autonomous checkout on the backs of ~$100M raised over the past 2 years. SC is focused exclusively on AI-powered checkout: SC enables autonomous checkout for brick and mortar retailers with an AI-powered computer vision platform.  In this episode, I chatted with Jordan Fisher (Founder/CEO of SC) and we touched on a number of topics, including: (1) the future of retail analytics and in-store experience, (2) the challenges of selling technology in a low margin industry, (3) how his technology differs from Amazon/why Amazon didn't create Go in stealth and take out all of the oxygen out of the room, (4) the implications of autonomous technology for global privacy standards and job creation/destruction and (6) ancillary possibilities that could be created as a byproduct of the SC technology at scale. 
57:53
March 30, 2020
45: Vlad Magdalin, Founder and CEO of Webflow
No code is a trend that has powered much of the internet since the days of Dreamweaver. However, in 2020, "no code" is making a come back at a stronger pace than ever before. The world operates on code, but only every 1 in 400 understand it; imagine if only every 1 in 400 people could write - the world would be an incredibly different place. This week we were joined by Vlad Magdalin, Founder and CEO of Webflow - one of the pioneers of the "no code" movement. Vlad recently raised $72M from Accel Partners to scale his vision into reality. We touched on a number of topics in this conversation - dealing with rejection in the early days, the irrationality to keep going when things looked bleak, how he grew to $20M ARR with limited outside financing, why he raised a monster round from Accel and why he believes this is the inflection point for "no code." At the end of the discussion, we finished out by talking about gratitude - Vlad came to the US as a refugee from Russia at 9; gratitude has shaped his outlook on privilege and the real priorities in life. This conversation was a ton of fun - a lot of the folks we have on the podcast are winning in an objectively massive way. Vlad is a genuinely good guy and it's awesome to see him specifically win. 
43:53
March 5, 2020
44: Rahul Vohra, Founder and CEO of Superhuman
Workplace communication predictions over the last 5 years has been dominated by the rise of chat apps like Slack and email ostensibly becoming eliminated. Yet email lives and thrives today - according to Radicati, nearly 300 billion emails are sent and received every day. The conversation around email - though such an important driver of workplace communication - has been stagnant. Enter Superhuman, the next generation email platform. Superhuman has gotten the attention of Silicon Valley’s most prominent and the levels of virality in this product mirror Slack and Dropbox in the early days. It was a pleasure to have Rahul Vohra, Founder and CEO this week; Rahul has raised $40M+ and is using that resource base to drive his uniquely quantitative perspective on evaluating product market fit - a topic we spent much of the discussion on. He also shared his perspective as to what holds for the future of email, why the enterprise will pay for products that have historically been free, and why he and his team are so well placed to compete with free from the 800 pound gorilla of email, Google.
47:17
February 23, 2020
43: Sara Mauskopf, Founder and CEO of Winnie
Childcare is fundamentally shifting - the share of households where both parents work hit 66% in 2016, up from 49% in 1970, according to the Pew Research Center.  Sara Mauskopf is the CEO and co-founder of Winnie (https://winnie.com), a marketplace for child care built on powerful data systems and backed by a trusted community of parents and providers. Parents use Winnie to discover high-quality local daycares and preschools and learn all about their programs including detailed descriptions, photos, tuition information, licensing status, availability data and more. Child care providers use Winnie to fill their open spaces, build their wait lists, and get support and resources to run their business efficiently. Winnie was started in early 2016 when Sara became frustrated with the long search to find child care for their young children. Now Winnie is used throughout the United States and is helping connect millions of parents with high quality child care. This conversation was one of the most genuine we've had on the podcast - Sara talked fundraising while pregnant, why Winnie is for ALL parents and not just moms, equality in the workplace and equality at home, and what keeps Sara down to earth maintaining perspective while running a high growth company.
34:36
December 5, 2019
42: Phin Barnes, General Partner at First Round Capital
There's a lot of noise in the venture ecosystem today on differentiation. When I think of a venture firm that defines differentiation, I think of First Round Capital. This week I chatted with Phin Barnes, General Partner at First Round, on a whole host of topics. Phin brings a unique operating background to the table - he spent six years helping to scale AND 1 Basketball from $15 million to over $225 million in revenue. - and has scaled this experience to a number of fantastic companies. In this conversation we discussed:  - Intentionality and why the best Founders have it (specifically he referenced Notion, Modern Fertility, Steady, Clearbit) - Initially working for free for First Round Capital with no intent to ever become a Partner - The importance of moving slow and challenging the cult of speed - Success being found in moments of discontinuity vs. continuity - Compensation for judgement vs. time - Tech enabled businesses vs. pure play software businesses (e.g. Peloton, WeWork) - Pattern recognition as a code for intellectual laziness  - Measuring learning on a "per dollar" basis - Why diversity isn't talked about enough and how he wants to change that 
53:12
November 26, 2019
41: Julien Smith, Founder of Breather
Julien Smith is one of the most direct, thoughtful and intense Founders I've had the pleasure of having on the show. Julien founded Breather in 2012 and has since raised $150M+ to build out the business. He's the New York Times bestselling author of three books. Two of these, Trust Agents and The Impact Equation, were written with Chris Brogan. The third, The Flinch, has consistently remained one of the top read Kindle books since it was published in 2011. Having Julien on the show was a pleasure - he's extremely original in thought and has some of the best content on the internet. We talked about his article "The Complete Guide to Not Giving an F", the importance of showing up, failing your way to the top, self awareness, and how we as a tech community can generally improve. This episode was a blast. 
51:07
October 18, 2019
40: Andrew D'Souza, CEO of Clearbanc
For an industry that has made its mark on funding disruption, venture capital hasn't changed much over the past 30 years. With new entrants (cue: Softbank) and discussions about venture dollars primarily pouring into real estate and customer acquisition, it has become more common to question whether venture capital is the right type of capital for all stages of a business. Why do we treat businesses as black and white binary entities? Equity or debt. That's it. Enter Clearbanc - Clearbanc is building an alternative capital source for entrepreneurs. The company has raised $300M+ and funded thousands of entrepreneurs. Andrew and I chatted about why Clearbanc is a truly differentiated source of capital, at what point is it most applicable and when does it become more preferable to traditional equity or debt.  Clearbanc's innovation has significant potential implications for the entire venture market. If you believe in the premise that equity capital is best suited to fund risk and experimentation and a new source of capital (a la what Clearbanc provides) is best suited to fund repeatable growth, a new asset class has the potential to right size how we think about segments of capital markets. Our conversation extended well beyond the nuts and bolts of the capital stack - we got knee deep into startup operations. We talked pivots (Clearbanc started the business focused on Uber drivers!), hiring, building in Toronto and the pros/cons vs. being based in Silicon Valley, unique operating practices at Clearbanc and why the company's culture is a mix of Lululemon and Bridgewater.
58:47
October 3, 2019
39: Auren Hoffman, CEO LiveRamp and SafeGraph
Today’s guest is Auren Hoffman, Former CEO of LiveRamp and current CEO of Safegraph. Auren has had one of the most storied careers of SaaS founders in the Valley and is known for having an often unique and contrarian perspective. In this conversation we discussed why the best businesses are at the intersection of value creation, personal advantage and a contrarian perspective; whether businesses should target niches or broad markets; and the advantages of being older as computing power becomes more powerful.
34:58
September 26, 2019
38: Elad Gil, Legendary Investor & Operator
Elad Gil really needs no introduction - he’s been integral in some of the most interesting and iconic companies in the valley. After fulfilling a PhD at MIT and a brief stint at McKinsey and Company, Elad went on to join Google and Twitter through their hypergrowth years; he joined Twitter when there were 90 employees and two and a half years later, he had helped the company scale to 1,500+. Elad is the founder and former CEO of Color Genomics and has invested in 20+ companies valued today at over $1B, including Airbnb, Coinbase, Checkr, Gusto, Instacart, OpenDoor, Pinterest, Square, Stripe and Wish. This episode was a ton of fun - I talked to Elad about his perspective on industry towns, why there aren’t many founders that come from Amazon, Microsoft, or Apple , his genomics research, how he evaluates companies and what are the most counterintuitive principles he taken away from investing in over 20 unicorns.
54:15
September 12, 2019
37: Mike Knoop, Co-Founder and Chief Product Officer of Zapier
In Silicon Valley today, it’s become a phenomenon to talk about raising less venture capital and going remote to offset capital cost and get better access to talent. This wasn’t always the dominant perspective; in fact it was often looked upon as an inhibitor to building a great company. Zapier - founded roughly a decade ago - has turned those two principles, amongst others on their head. Today the business has (still!) raised less than $1.5M, just recently crossed $50M in ARR and has been fully remote since Day 1. This episode was a ton of fun - I talked to Mike about how him, Wade and Bryan founded the company, their original vision for the business and how it has transformed a decade later, and how they have successfully led a remote company. Mike’s authenticity is audible in his voice - it was great to hear his very candid and humble perspective on building a once in a generation company.
43:03
September 4, 2019
36: Steve Schlafman, Partner at Primary Venture Partners
You don’t have to search high or low in the tech community to find tips and tricks on every function in a business - product, engineering, fundraising - it’s all out there. Only recently have mindfulness, leadership and mental health become top topics that founders and investors have started systematically talking about. In this episode I talked to one of the best advocates of mental health and coaching in the tech community today - Steve has a unique perspective on coaching early stage founders and we talked about the challenges and opportunities in the space. Steve is a trained executive and performance coach. He works with founders and executives to help them fulfill their potential as leaders inside and outside their organizations. Steve decided to pursue a coaching certification because he had a strong desire to engage with founders more deeply and develop stronger relationships based on respect, trust, authenticity and vulnerability.  Steve’s words are important for all folks in the tech community to be better leaders. Steve has had a storied career as an investor. He has been investing in the NYC tech ecosystem for the last decade. He straddles B2B and B2C with a bias toward the weird. His human centric approach to investing has enabled him to lead investments in Giphy, Bowery Farming, Brightwheel, Groups, Boom Aerospace, Care/of, Citizen, Wag!, theSkimm, Breather, View The Space and many more.  This episode was a ton of fun - Steve's authenticity is audible in his voice. It's no question why he's been such a great champion for founders. 
59:13
July 31, 2019
35: Paul Arnold, Founder and General Partner of Switch Ventures
Data driven venture capital is a controversial topic with strong opinions attached. The classic rebuttal of data driven VC is the idea that successful early stage startups look wildly different and so even if you do capture clean data, there is a fundamental skew (e.g. either you misplace predictive importance on certain variables or your data set is not large enough) so the outcomes would be falsely comforting. On the other side of the coin, however are venture firms that have not only positioned themselves as data oriented firms, but have broken through this narrative and realized outstanding returns as a function of this orientation.  Enter Switch Ventures. A seed stage venture fund focused on identifying the most talented startup entrepreneurs through data science. Paul Arnold, founder of Switch, has longstanding experience applying data driven strategies with C-Suites, Boards and front line employees to drive change. He was a senior executive at AppDirect and helped build it into the unicorn it is today; prior to AppDirect, Paul was with McKinsey & Company in Silicon Valley.  It was a pleasure to have Paul on the podcast. We talked about a number of topics in this episode. Some of my favorite, included: (1) the early days of Switch, (2) his data driven investment approach, (3) how his approach has evolved as he’s gained more experience as an investor and (4) where he believes the future hubs of innovation will be.  Follow Paul’s writing on Forbes and get in touch with his team at Switch if you’re building a company and interested in his approach. 
26:02
June 20, 2019
34: Peter Reinhardt, Founder and CEO of Segment
The rise of SaaS has liberated the enterprise stack. Products are now brought into an organization at the atomic level and decentralized decision making has enabled modern tech companies to move incredibly quickly to solve specific problems. The challenge of this speed however is the complexity that a web of unrelated applications creates.  Glossier, a recent entrant to the unicorn club, uses 14 different analytics tools across 12 different platforms such as their website, their mobile app and their brick-and-mortar store. Each tool has its own copy of the customer data and history of privacy preferences; the complexity to uncover key insights becomes an impediment to how effectively a business can operate.  Enter Segment. The analytics tool to end all integrations. Segment has raised over $250M from leading investors including Accel, Google Ventures, Y Combinator Continuity Fund and Thrive Capital. Segment raised its Series D ($175M) last month and the venture community is excited about the company being the defacto layer of stitching together disparate customer data for organizations.  It was a pleasure to have Peter on the podcast. We talked about the early days of Segment, pivoting with only $100K left in the bank and scaling a business that has now raised over $250M. Some of my favorite moments included: (1) how Peter thinks about speed vs. process at different junctions of growth, (2) the characteristics of true product market fit, (3) how Peter has shifted his time as the company has scaled and (4) the unique value system that has been implemented at Segment. 
37:29
May 16, 2019
33: Ash Fontana, Managing Director at Zetta Venture Partners
“Data is the new oil” has become one of the most common catch phrases in popular media. It makes sense right? Wrong. At least according to Ash Fontana, Managing Director at Zetta Venture Partners and one of the most nuanced thinkers on AI today.  Ash believes we are squarely in the fourth era of computing, the intelligence era. In this era, data aggregation is less interesting than matching data sets to tactical problems. And with good reason. The intelligence era is an inflection point; traditional I.T. infrastructure will change to enable the development of self-learning software and previously data-starved markets — from agriculture to sales — will benefit from the information generated by self-learning software.  Ash thinks about AI companies with an incredibly human centric approach; when he evaluates data sets and companies, he asks how much human activity can the company free up if it works at scale.  In this episode, we chatted all things AI with Ash. We talked about a number of topics; some of my favorite included: (1) the utility of data for AI first companies, (2) why data strategy is fundamentally different for an AI driven company vs. a normal software company, (3) why Ash is bearish on SaaS and (4) how do you compete with Google, Amazon and Facebook in a data driven world. It was a pleasure to have Ash on the show to get his thoughts on the future of AI. His perspective was incredibly thoughtful and I personally learned an incredible amount from him in this conversation. 
53:14
May 2, 2019
32: Brianne Kimmel, Managing Partner at Work Life Ventures
Joe Rogan gets more views than CNN. Kylie Jenner is dominating cosmetics (with less than 30 employees). Conor McGregor can sell more PPVs than UFC. So what’s going on? The labor markets we are living through today are at an inflection point. The age of the individual is on the rise and AI is automating away “old world” jobs, while increasing leverage for “new world” jobs. The McKinsey Global Institute did a study on looking at characteristics and occupations that could be automated away; the conclusion was that we are in for a significant shift over the next 20 years. This week I chatted with Brianne Kimmel on all things future of work.
48:15
February 28, 2019
31: Brynn Putnam, Founder and CEO of Mirror
We are notorious as a society for falling in love with the next “fitness fad.” Whether its diet types, workout regimens or new fitness equipment, we’re suckers for “quick fix” schemes. It’s pretty rare that we come across a product that revolutionizes the way we workout — and in the age of connected hardware and software — we’re living through a paradigm shift that allows us to reimagine the fitness experience from first principles. This week, I got the chance to chat with Brynn Putnam, Founder and CEO of Mirror, a connected fitness system that streams live and on-demand classes to users in-home via a sleek responsive display. Mirror enables users to train with experts, work out with friends and get real-time personalization. The confidence from the venture community for Mirror runs deep — the company has raised $40M+ from leading investors, including Spark, First Round, and Box Group — and it’s easy to see why. The market is huge, the product is fantastic and Brynn is an incredibly thoughtful leader. I found many of her reflections insightful; specifically it was most interesting to hear her talk about: (1) running a combined hardware, software and content business, (2) thinking about the business as a “media company” vs. a “technology company” and (3) the pathway to evolve Mirror from a fitness business into “the defacto screen in your life.”  It was a pleasure to have Brynn on the show to get her thoughts on the future of connected home. This is going to be a fun company to follow. 
27:44
February 21, 2019
30: Shaan Hathiramani, Founder and CEO of Flockjay
The future of education and skilling is becoming very interesting. When you apply first principles thinking, the classroom experience, curriculum and economic model are all up for grabs. This week I chatted with Shaan Hathiramani, Founder and CEO of Flockjay, a 12 week immersive online sales academy that only charges students IF they secure a $50k+ job upon completion of the program.  We hear a lot about bootcamps in tech and the idea of the income share agreement is becoming a more popular way to align incentives, but we have yet to see these concepts married together for sales. So what inspired Shaan to start the company? He spoke with 250 universities and asked them a simple question “Did they have any courses that teaches anything related to Salesforce?” A resounding “no” empowered his belief that college curricula and the necessary skillset to be productive in the marketplace was out of balance. I got a chance to learn more about Flockjay’s current cohort and the backgrounds of the students are incredibly inspirational. Some are first generation Americans, some have done tours in Afghanistan and some grew up in foster care. The coolest part about Flockjay is it works for all demographics, all ages and all backgrounds. All you need is grit. It was a pleasure to have Shaan on the show to get his thoughts on the future of skilling. Watch out for this company — Flockjay is going to be really interesting to watch over the next decade.
45:18
February 13, 2019
29: JD Ross, Co-Founder of Opendoor
The global stock of institutional grade real estate is set to triple over the next 15 years, with some estimates pegging aggregate values at ~$70 trillion. With this increase in asset volume, there’s a slew of complexity and change on the horizon — social migration will change the distribution of construction, the changing nature of cities presents a wider range of risk and return opportunities and technology is playing a deeper role in we re-think the physical world. Though there’s significant macro change on the horizon, participating in the market today feels less than inspirational — transacting is expensive, messy and lacks transparency.  Enter Opendoor. Opendoor brings machine learning and a thoughtful user experience to bear to dramatically simplify the end-to-end residential real estate transacting process. The company has raised $500M+ over the past few years and has scaled to 1,000 employees in less than half a decade. JD and I chatted at length about: (1) the technological shifts that make Opendoor possible, (2) key lessons he’s learned in scaling a business so quickly, (3) the flywheel effect for Opendoor and why its different from other marketplace businesses, and (4) the challenges incumbents face in entering this space. It was a pleasure to have JD on the show. 
34:05
February 6, 2019
28: Brent Beshore, Founder and CEO at adventur.es
In an age of speed, overstimulation and FOMO, it’s easy to get caught up in the latest tech trend. This mindset doesn’t discriminate and is often most pervasive amongst the most sophisticated people in the world. Over the past year, I’ve had a number of conversations with Fund LPs and often I hear comments like “What crypto investments should we make?”, “When will VR take off?” and my favorite “Did this fund invest in a scooter company yet?” It would be naive to write off any of those sectors and think that massive value won’t be created by the winners in those spaces. What I find most interesting though is how little airtime we give to the massive sector of value creation that lives and breathes on the complete opposite side of the spectrum. These are not the businesses that will 10,000x their value in 5 years, but they are ones that print material and consistent cash flow over outsized periods of time. Or as our guest in this episode likes to call them: “boring businesses.”  Brent Beshore is the Founder and CEO of adventur.es, a extremely unique PE firm in Columbia, Missouri. Brent has raised $50M of capital for his fund and partners with entrepreneurs with the intention to never sell his ownership stake. We chatted at length about boring businesses, evaluating fads vs. trends and some of his biggest philosophical learnings from looking under the hood at over 12,000 companies.  It was a pleasure to have Brent on the show. He’s undoubtedly a sharp investor, but he has a refreshing amount of empathy which I appreciate the most.
52:38
January 29, 2019
27: Ali Hamed, Managing Partner at CoVenture
“First principles” thinking gets a lot of lip service today in technology and venture capital. While its in vogue to acknowledge this way of thinking, very few actually adhere to it in practice. In this episode, I chatted with Ali Hamed, Managing Partner at CoVenture — one of the most “first principles” thinkers I’ve had the privilege of speaking with and hosting on the show.  In this episode, Ali opened up what is possible when you think creatively — whether its how to structure a firm across multiple asset classes (lending, venture capital and crypto), invest in new digital asset classes (e.g. rolling up Instagram accounts) or evaluate a company’s progress (debunking the fallacy of MRR and growth thresholds necessarily indicating progress). Ali covered it all in this conversation.  It was a pleasure to have Ali on the show. He pushed my thinking through the conversation and I learned a lot from him. 
50:52
January 23, 2019
26: Leo Polovets, General Partner at Susa Ventures
As software eats the world, the idea of moats and the power of compounding have taken a new turn of influence. I chatted with Leo Polovets, General Partner at Susa Ventures on the importance of these two fundamental concepts and why they are so powerful, but yet still so counterintuitive in 2019. In this episode, Leo expanded on his experience from being one of the first dozen employees at LinkedIn to experiencing hypergrowth at Google and how this has enabled him to find and support the next set of generational companies, e.g. Robinhood, Flexport, Andela and LendUp. He expanded on Susa's investment thesis in funding entrepreneurs that are building highly defensible companies that leverage data, economies of scale, and network effects to build value and achieve longevity. We also touched on nuanced philosophical concepts in company creation such as "position vs. momentum" and "ego vs. perception." It was a pleasure to have Leo on the show. He's one of the most thoughtful venture investors I've had the privilege of getting to know.
43:19
January 10, 2019
25 Harry Ritter, Founder and CEO of Alma
Today, the mental health crisis has reached a tipping point - one in five adults has a mental health condition and over the last 20 years there has been a 30% increase in suicide rates and 130% increase in depression amongst young adults. From a economic perspective, we're facing a staggering ~$200 billion in lost earnings (per annum) attributed to mental illness.  In many ways, there are troubling signs that these numbers will actually get worse - these conditions are further exacerbated by two phenomena: (1) uneven access to mental health services (the Mental Health America study found that 50+% of Americans don't have access to basic services) and (2) the stigma against mental health (many don't get the care they need even if they have access, because of the associated label).   Despite the sheer size and growing demand for services, (e.g. over 2.5 mental health providers for everyone one primary care physician and a labor market growing 25% per annum), the space is incredibly fragmented and underserved. NYC alone has a staggering 90% of its providers working as solo practitioners. The lack of sophistication, quality of user experience and shortages that follow sub-scale practice add up. In this episode, we unpacked all these dynamics and how software and design play a pivotal role in improving the patient and provider experience with Harry Ritter, Founder and CEO of Alma. Alma is a new practice model for therapists designed to elevate the therapy experience and simplify access to great care. It was a pleasure to have Harry on the show to discuss this distinctly important topic.
40:31
November 23, 2018
24: Jack Altman, Founder and CEO of Lattice
The last decade has seen significant change across virtually every function in business; the evolution of marketing, sales, customer success, product and operations departments has been tremendous. HR on the other hand, has been a laggard; historically a back office cost-center, typical HR organizations have followed the mandate of being compliant, administrative and "doing less." However in 2018, this is all changing. In a world where the leverage in the "war for talent" has shifted to employees, HR is becoming a strategic asset; companies are understanding more and more they are above all in the people business. This mindset shift has pushed HR to focus on employee experience, improving engagement and overall organizational health.  In this episode, we unpacked all these dynamics and how software plays a pivotal role in the new HR world-order with Jack Altman, Founder and CEO of Lattice. Lattice offers an elegant user experience on the front end with a rigorous data engine on the back-end to help organizations drive best in class performance management. It was a pleasure to have Jack on the show.
45:49
October 30, 2018
23: Bradley Tusk, Founder and CEO of Tusk Holdings
In 2018, Uber is a household verb. The company is on an absolute tear; Dara Khosrowshahi has assembled a world class management team and Uber is evolving from a ridesharing company into a full scale transportation business. The company now has multiple business units at multi-billion dollar run rates; earlier this year Uber announced Eats is at a $6B+ bookings run rate. Excitement around the company is steep and in 2019 we are likely to see an IPO. The early view on pricing is Uber will enter the public markets at $100B+ market cap. Back in 2011 however, Uber was anything but a foregone conclusion. The company had raised a small Series A and the incumbent taxi industry threw everything they had at the business. Fights were prevalent in every market, but the battle in New York City was especially high stakes. The world was watching New York and if Mayor DeBlasio succeeded in shutting Uber down, it was only a matter of time before the rest of the world followed. Founder and then-CEO Travis Kalanick engaged Bradley Tusk to help with the fight. One of the most public and epic battles between private enterprise and city hall, Bradley ran a genius political campaign that ultimately kept Uber up and running as a business. We unpacked how it all went down in this episode.  It was a pleasure to have Bradley on the show; we spent most of the time chatting about Uber, but we also touched on how he's using blockchain to empower mass mobile voting - a key initiative to fix low voter turnout - and whether his former boss Mike Bloomberg will run for President in 2020.
49:26
October 18, 2018
22: Austen Allred, Founder and CEO of Lambda School
Education is broken. Since 1996, only three sectors have materially risen when adjusted for inflation. Construction is a bit more expensive than the inflation benchmark, healthcare and childcare prices have risen ~2x the benchmark, and college education has risen 4x inflation!  This rising cost is having a significant impact on the economy - millennials are less likely to start businesses, own homes and are taking longer to "settle down" due to the crippling impact of student loans.  A lot of companies have been trying to disrupt the higher ed space; one of the companies I've been most impressed by in the space is Lambda School - a 30 week immersive coding school that only charges students IF they secure a $50k+ job upon completion of the program. Lambda is one of the fastest growing startups in the Valley and just announced a fresh round of capital this week, led by Google Ventures and Stripe.  It was a pleasure to have Austen on the show to get his thoughts on the future of education. Watch out for this company - Lambda has the potential to be one of the most important and impactful companies in the next 20 years.
38:11
October 10, 2018
21: Morgan Housel, Partner at Collaborative Fund
One of my favorite writers (and thinkers) in tech today is Morgan Housel. Morgan consistently puts out some of the most provocative thought pieces and draws connections that routinely leave me wanting more. This week, it was a thrill to chat with Morgan. We touched a number of topics across philosophy, investing and psychology. Unlike many of our other episodes, I didn't have a few "favorite moments" - the entire conversation was filled with nuance and timeless perspectives.  Also check out these pieces from Morgan that we referred to in the conversation: The Psychology of Money, Immeasurably Important, The Lifecycle of Greed and Fear, Tails You Win, Useful Hacks. You can read Morgan's other articles and subscribe to his writing on the Collaborative Fund blog.
48:25
August 26, 2018
20: Omar Tawakol, CEO of Voicea
One of my favorite pieces for how to think about technology platform shifts is Chris Dixon's "What's Next in Computing". Chris notes that if we look at history, we see that irrespective of the way financial markets perform, technology platform shifts happen consistently every 10–15 years.  One of the most important platform shifts of the next decade is voice. Consumer markets have started to appreciate the strength of Alexa, Echo and Google Home but the recent demonstration of Google Assistant at Google I/O 2018 really expanded the imagination for what will be possible in a decade as deep learning and natural language exponentially improve.  Lately, I've been incredibly interested by the impact voice will have in the enterprise. This week, it was a thrill to chat with Omar Tawakol, one of the key players in today's enterprise voice landscape. Omar is the CEO of Voicea, a voice-activated AI for the workplace; he's raised $20M to leverage AI to augment tasks, make meetings more productive and create more efficient workflows. Eva (Voicea's AI-assistant) in actionPrior to Voicea, Omar was the founder and CEO of BlueKai which built the worlds largest consumer data marketplace and DMP. Oracle acquired BlueKai in 2014 & Omar led Oracle Data Cloud where he scaled the team to over 1,000 people and pioneered the ODC to become the leading Data-as-a-Service provider to 96 of the top 100 US marketers. Omar earned an MS in CS from Stanford (BS, MIT) where he researched and published work on AI agents. Check out the conversation and our other episodes on iTunes.
35:38
July 1, 2018
19: Megan Quinn, General Partner at Spark Capital
Coinbase. Slack. Affirm. Wealthfront. Medium. All generational companies with general founders. Each of these companies has gone on to become valued at $1B+ and have created lasting impact in their respective industries. As a venture investor, becoming involved with any one of these companies would be considered a grand success. Megan Quinn, GP at Spark Capital, has been involved with all of them. It was a thrill to chat with Megan. Aside from a successful investing career with both Kleiner Perkins, where she led a number of the firm's early-stage and growth consumer investments, and Spark Capital, Megan was an operator at both Square and Google. As Square's Head of Product, she led strategy and development of the company's products across merchant and consumer audiences. At Google, Megan spent seven years at Google where she held various leadership positions in marketing, business development and product management. She oversaw the development and launch of some of the company's most successful products, including Google Maps.  This conversation was a ton of fun. Megan and I discussed a number of topics including: (1) her infamous rise to Head of Product at Square (just 2 weeks after being hired in as Director of Risk), (2) her fascination with maps and her time at Google leading the Maps team, (3) investing in Coinbase and her outlook on crypto and (4) her important work as co-founder of the non-profit AllRaise.
45:10
May 30, 2018
18: Hayley Barna, Co-Founder of BirchBox and General Partner at First Round Capital
Almost exactly a decade ago, a new bright eyed class of students entered Harvard Business School in September 2008. One month in, something happened that nobody could have anticipated: the economy completely fell apart. The world experienced the worst financial crisis since the Great Depression. At a time where the future looked uncertain and bleak and taking career risk was probably the last thing on any rational person’s mind, something magical happened at Harvard Business School. In just a short time window the foundation for multiple multi-billion dollar companies was being laid: Rent the Runway, Blue Apron, Plated, StitchFix and BirchBox.  This week I caught up with Hayley Barna, co-founder of BirchBox and current General Partner at First Round Capital. One of the famed consumer success stories of the last decade, BirchBox revolutionized the application of the subscription e-commerce business model to beauty and retail. Hayley helped the company raise over $80M in venture capital, generate $100M+ annual revenues and deliver products into the hands of over 1 million monthly subscribers. In her current role at First Round, Hayley is focused on finding the next crop of great consumer companies.  We had a lot of fun in this one — Hayley is one of the most personable guests we’ve had on the podcast. The conversation is filled with great lessons, but a few highlights included: (1) why the downside of taking risks is overrated, (2) how impact at scale is all about people and culture, (3) the importance of balancing growth with sustainability and (4) Hayley’s belief that the best thing you can do for yourself is “just getting out there and doing it”.
43:28
March 22, 2018
17: Andy Rachleff, Co-Founder Benchmark Capital and CEO of Wealthfront
“Product-market” fit is one of the most ubiquitous and foundational terms in the startup community today. It’s a term that has inspired blog posts, books, curriculums, conferences and even plot lines of TV shows (turns out, its just as hard to find product-market fit in TV land). It’s virtually impossible to talk about products today without hearing reference to product-market fit; there are 400,000+ unique results on Google and over 5,000+ videos on YouTube explaining the concept.  It was a thrill to speak with the legendary executive and investor who coined the term, Andy Rachleff. Andy co-founded Benchmark Capital and led the single best performing early stage fund of all time. Benchmark has invested in an absolutely dynamite list of startups over the last 20 years: eBay, Uber, Twitter, Snapchat, Dropbox, Instagram, WeWork, StitchFix, Yelp, Zendesk, and Zillow amongst others. Over the past decade, Andy switched back to the operating side and founded Wealthfront. Today Wealthfront is the leading automated investment service in the market with over $10 billion in assets under management. We had a lot of fun in this one. This conversation was highly focused on Andy’s foundational work in product market fit, disruptive innovation and how these concepts serve as guiding principles in his work today with Wealthfront. The podcast is filled with great lessons, but a few highlights included: (1) why you can screw up everything if you have product market fit and still likely succeed, (2) how the best companies are founded with insight to a key inflection point in technology, (3) why the combination of being correct and contrarian drives the highest potential for value creation and (4) why failure is overrated.
35:22
February 10, 2018
16: David Tisch, Managing Partner at BoxGroup
Very few individuals in the startup community have seen deep success as operators, investors and community builders — it’s why this week I was so excited to chat with David Tisch. David is the Managing Partner of BoxGroup, an early stage venture fund in NYC; via BoxGroup, he has invested in a number of fantastic companies — GroupMe, Trello, ClassPass, Warby Parker and Harry’s amongst others. He also is the Founder and current Chairman of Spring, an e-commerce platform that recently raised $65M from Fidelity as well as the Head of the Startup Studio at Cornell. All three of his current roles, as well as his prior role in founding Techstars NYC give David a deep and thoughtful perspective on startups and technology.  We talked about a number of topics in our conversation related to the state of venture, startups and careers. Some of the most interesting perspectives David had centered around: (1) how technology has moved from a vertical to a horizontal, (2) what NY has doubled down on and how it has propelled to become a world class innovation hub and (3) how defining yourself is about more than just your pedigree.
37:33
January 20, 2018
15: Jerry Storch, Former CEO Toys R Us and Vice Chairman of Target
“Amazon is eating the world” is today’s conventional take for retail outsiders. It’s certainly a position I espouse and it’s why this week I was so excited to chat with Jerry Storch. Jerry most recently was the CEO of Hudson’s Bay Company and previously was CEO of Toys R Us and Vice Chairman of Target. Jerry is known in the world of retail for his forward thinking on technology and has embraced technology heavily as a Senior Executive. At Target, he founded and led the e-commerce strategy of target.com, at Toys R Us he expanded the e-comm business to over $1 billion and led international expansion into China, and at Hudson’s Bay he drove the acceleration of the all-channel e-comm business model.  We talked about a number of topics in our conversation related to technology and retail, leadership and careers. Some of the most interesting perspectives Jerry had centered around: (1) the importance of thinking through big bets via first principles, (2) why the debate around AI and it’s impact on society should be reframed to a short term discussion on displacement and a long term discussion on growth, and (3) how learning in 2017 is all about being a maniacally vociferous reader. 
44:04
December 17, 2017
14: David Fialkow, Co-Founder and Managing Partner at General Catalyst Partners
Snap. Warby Parker. Airbnb. Stripe. Kayak. That list of companies has a two clear things in common: (1) they are all generational companies that have contributed to significant value creation and (2) General Catalyst invested in all of them. This week, we dug deep into what’s going on in the world of venture with David Fialkow, Co-Founder and Managing Director at General Catalyst. David had an interesting journey to venture — successfully founding and exiting four companies — and ultimately created an early-stage fund to give the type of support to entrepreneurs he sought as a founder. My favorite moments in this conversation included David’s reflections on: (1) how to think about aligning founder and VC interest, (2) why going public is overblown and (3) why at the end of the day, nothing matters more than people .
23:08
November 19, 2017
13: Jason Lemkin, Managing Director at SaaStr
Venture capital is hard. Startups are brutal. The media has turned the winners of innovation into mythical heroes often glorifying the end result over the struggle of the process. Is this good or bad? What are the implications for the broader tech industry? What about for the hordes of individuals encouraged to enter a race where the odds are stacked against them? This week I had a fiery and candid conversation with Jason Lemkin on these very topics. Jason is a SaaS legend - he's a 2x successful founder, current Managing Director at SaaStr Fund, and runs SaaStr Annual, a community of over 10,000 founders, investors and executives focused on B2B SaaS.  This conversation was candid as ever and Jason debunked the ease that startups and venture capital are often portrayed with. My favorite moments included: (1) the importance of atomized thinking when it comes to tackling challenging problems, (2) the inherent challenge for big companies in sustaining and supporting innovation and (3) why your team is the most important decision you can make as a founder.
39:11
November 5, 2017
12: Keith Rabois, General Partner at Khosla Ventures
Hiring correctly and operating proficiently are two of the most complex and nuanced management skill sets necessary to lead an organization to success. This week, we dived into these topics much more deeply with Keith Rabois, General Partner at Khosla Ventures. Keith is a member of the famed PayPal Mafia — having worked closely with Peter Thiel, Elon Musk and Reid Hoffman amongst others in his early days — and has become a revered source of how to successfully hire and execute in Silicon Valley. Keith held Executive roles at PayPal, LinkedIn, Slide and Square prior to joining Khosla Ventures.  This conversation was a ton of fun and we talked through a bunch of different topics, some of which included: (1) how to think through hiring and retaining talent, (2) the characteristics of world-class leaders and (3) the need for organizational transparency and laser-pointed focus at the highest levels. One of my favorite parts of the conversation was our “lightning round” at the end, where Keith gave his thoughts on which of today’s largest tech companies will be least influential in the future, whether or not Silicon Valley remains the world’s innovation hub going forward, and the best pieces of advice he ever got from Peter Thiel, Elon Musk, Reid Hoffman, Vinod Khosla and Jack Dorsey.
39:49
October 15, 2017
11: Jim Feuille, General Partner at Crosslink Capital
This week I chatted with Jim Feuille, General Partner at Crosslink Capital. Jim joined Crosslink after a successful career in finance, previously serving as Global Head of Technology Investment Banking at UBS. Over the past 15 years in venture, Jim has invested in successful teams at Omniture, Ancestry.com, Coupa and most notably, Pandora. Jim and I covered a number of topics in this one; ranging from Pandora and the state of the consumer internet in 1995 to capital allocation in venture today and what new entrants (i.e Softbank and their $100bn Vision Fund) are thinking. Some of my favorite moments included: how the Crosslink team was able to source Pandora (11:55), why the freemium model was core to Pandora’s rapid growth (18:40) and what he thinks of capital allocation and valuations today (23:20).
42:57
October 9, 2017
10: Brad Jones, Founding Partner at RedPoint Ventures
Product. Market. Team. Though a significant amount has changed in venture over the past two decades, the focus on these three variables has still remained largely the same when it comes to investing. This week, I chatted with one of the most successful venture capitalists of the past two decades, Brad Jones, Founding Partner at Redpoint.  Brad co-founded Redpoint in 1999 after serving as a General Partner at Brentwood Venture Capital. Over the past 20 years, Brad has served on the boards of over 10 public companies and his team has invested in household names like Stripe, Twilio, Zendesk, Fortinet, Heroku and early on, Netflix.  Brad and I spoke for about an hour and covered a number of topics in this one; we talked about startups, the state of venture capital and where we’re headed. Some of my favorite moments included: why less companies going public is bad for retail investors and broader society (17:20), his observations on how starting and scaling a startup has changed over the past 15 years (21:44), what he thinks of the state of culture in the technology community today given the recent turmoil at Uber (25:46) and ideas for how local and national government can help startups (43:21).
56:22
June 24, 2017
9: David Golden, Managing Partner at Revolution Ventures
High-growth companies can now start and scale anywhere, not just in a few coastal cities. This is the fundamental premise of Revolution Ventures, the $200M venture capital firm started by AOL, Inc. founder Steve Case. This week, I chatted with David Golden, Managing Partner at Revolution.  David joined Revolution after 18 years with JPMorgan. During his tenure at JPM, David held a number of roles, including Vice Chairman and Director of JPMorgan’s global investment banking practice for Tech, Media & Telecom. Throughout his career, David has served on the boards of a number of successful companies, including Everyday Health, Barnes & Noble Education and Blackbaud.
52:36
May 7, 2017
8: Ed Colloton, Managing Partner and COO of Bessemer Venture Partners
Bessemer Venture Partners has long been regarded as one of the most successful and influential venture capital firms in Silicon Valley. The firm has invested in a number of winners over the years including: LinkedIn, Yelp, Blue Apron, Periscope, Twitch, Shopify, Twilio and others. In our ninth episode, it was fun to chat with Ed Colloton, Managing Partner and COO over at BVP. Ed has had a very successful career both in PE and VC; he served as COO of JP Morgan’s Private Equity arm before transitioning to Bessemer where he has been recognized on the annual Forbes Midas List as one of the top 100 venture capitalists globally.  Ed and I spoke about a number of topics in this one; namely, what’s the future of VC look like, why less companies are going public, and what makes Silicon Valley special. My favorite moments included: (1) his thoughts on PE vs. venture as an asset class (21:54), what the ramifications of less companies going public are for society and innovation (27:11) and given his experience in Silicon Valley how he thinks about clean sheeting a plan for a city to become an innovation hub (32:31).
48:48
April 27, 2017
7: Chris Kelly, Former Chief Privacy Officer of Facebook and Co-Owner of Sacramento Kings
There aren’t many companies in the history of the world that have had as much of a global impact as Facebook. That’s why it was especially gratifying to chat with Chris Kelly, Former Chief Privacy Officer and Head of Public Policy at Facebook. Chris had the unique perspective of working at Facebook in the early days as one of the first 25 employees to being a key executive in a 1,000+ employee organization by the time he left in 2009. We had a lot of fun in this one and Chris and I spoke about a whole host of topics: his experience at Facebook, thoughts more broadly on what’s going on in the tech community, and the intersection of government, tech and the future of innovation in the US. Some of my favorite moments included: (1) his reflections on what it was like working with Mark Zuckerberg and how to think about culture (16:20), (2) what he thinks the next wave is in tech and whether its IoT, AR or VR (26:10) and (3) how to think about managing the downsides of emerging technologies, namely fake news (30:30)
54:14
April 23, 2017
6: Ben Alden, General Counsel of Betterment
It’s no question that AI is going to have an extremely large impact on our society. Like “the cloud” five years back, today machine learning is starting to become a common household word. In our sixth episode, I had the chance to chat with Ben Alden, General Counsel of Betterment and we dove into all things disruptive innovation in the wealth management space. Betterment has raised over $200m and manages more than $7bn assets globally. It is one of the darling stories of fintech (having been previously referred to as the “Apple of Finance”) and has a number of exciting future products in store for a rapidly growing trillion dollar industry. Ben is a native of Cornell University and Stanford Law and practiced as a Litigator at Sullivan & Cromwell amongst other roles prior to serving as GC at Betterment.
49:22
April 8, 2017
5: Chad Ho, Senior Vice President and General Counsel of Hulu
Chad Ho is Senior Vice President and General Counsel of Hulu. Chad’s had an interesting career in the entertainment space and has seen the highs (and lows) of multiple startups; he was employee #70 at MySpace and saw the website become the #1 most visited site on the internet and grow to 1,200 employees within a few years only to see it brought right back down to earth as Facebook came in and took over the space. Around that time he moved on and joined a then unknown and unnamed company as its General Counsel — fast forward a decade and that company has become Hulu, a global household name doing $1bn+ revenue annually.
42:49
March 4, 2017
4: Andrew Yang, Founder and CEO of Venture for America
Andrew Yang is Founder and CEO of Venture for America, a fellowship program for enterprising recent college graduates to launch their careers as entrepreneurs and revitalize American cities. Andrew has accomplished a lot with VFA since founding it in the last 6 years and has been a tireless advocate for entrepreneurship. He’s spoken at length on the subject, appearing on CNN, CNBC, Time, and the Wall Street Journal. Andrew was named a Presidential Ambassador for Global Entrepreneurship by the White House and one of Fast Company’s 100 Most Creative People in Business for his work with Venture for America. This conversation was a lot of fun; Andrew really humanized entrepreneurship and how to get comfortable with the uncomfortable. Some of my favorite moments included: (1) why entrepreneurship isn’t a magic trick (3:05), (2) how he sees entrepreneurship shaking out over the next decade (16:55), (3) the consciousness that has emerged from this election cycle (24:06), and finally (4) key takeaways for young professionals (40:01).  Check out Andrew’s awesome book “Smart People Should Build Things.”
44:21
February 21, 2017
3: Patrick Chung, Founder and General Partner at xFund
Patrick Chung is Founder and General Partner at Xfund, a $50M seed stage venture fund based in Silicon Valley. Patrick is an incredibly sharp guy; he has had an impressive academic career — with three degrees from Harvard University (College, Law School, and Business School) and one from Oxford University — and professional career, having been a consultant at McKinsey, operator at venture backed Zefer, and General Partner both at NEA and xFund.  This conversation was fun and Patrick gave a lot of interesting insight. Some of my favorite moments included: (1) why he thinks liberal arts founders thrive and his fund is a bet on that (6:05), (2) how an influx of capital affects seed stage investing (14:13), (3) why managing uncertainty will be a key strategy in 2017 (20:24), and finally (4) three key takeaways for young professionals (35:22).
37:54
January 8, 2017
2: David Hornik, General Partner at August Capital
David Hornik has a reputation in venture as one of the nicest and sharpest investors out there. He received Deloitte’s 2013 Venture Capitalist of the Year award and has been honored by Forbes Magazine as a member of its Midas List of top Venture Capitalists. This conversation was fun and David gave a lot of interesting insight. Some of our favorite moments included: (1) what he thinks of the current state of venture (11:05), (2) his adamant belief that we are not in a bubble, though things are overheated and overfunded (17:05), (3) the importance of making others successful and being generous (24:01), and (4) focusing on a happy life, not a successful career (30:10). David colored a lot of these insights via personal anecdotes of times with Jerry Yang, DJ Patil, Dick Costolo, Paul Graham, Reid Hoffman, Travis Kalanick and others.
36:24
December 11, 2016
1: Jim Koch, Founder and Chairman of Boston Beer Company
Jim Koch is the billionaire Founder and Chairman of Boston Beer Company (maker of Sam Adams). Jim is an incredibly sharp operator and is revered as the founding father of the American craft brewery movement. Born into a middle class family in Cincinnati, Ohio, he spent a formative decade of his life in Cambridge, earning a BA, JD, and MBA from Harvard. After 6 years as a Consultant at the Boston Consulting Group, Jim took a risk, quit his job and started selling Sam Adams. Today Boston Beer Company has annual revenues of ~$1 billion and sells more than 50 types of beer all over the world. Romeen and Jim discussed his early life, how he made the decision to start Boston Beer Company, and the key lessons he picked up across his career. Jim had many interesting insights, but a few that resonated most were: (1) get out of your echo chamber when making decisions (8:05), (2) laser focus your early career on developing skills (20:36), and (3) always be selling (24:44).
35:37
November 12, 2016