Shows
"Request for Startups" with Erik TorenbergCarta for Mainstreet, Consulting in the Age of AI, & the next GLG with Romeen ShethToday’s episode of Request for Startups features* Romeen Sheth: CEO of Metasys Technologies. @RomeenSheth on X* Erik Torenberg: Investor, Founder of Turpentine.co. @eriktorenberg on X* Sean Linehan: CEO of Exec.com, previously VP Product at Flexport. @seanlinehan on XIn this conversation, recorded in mid-2023, Romeen Sheth, CEO of Metasys Technologies, joins Erik Torenberg and Sean Linehan to discuss the potential of blended AI and offshore labor for service businesses, his ideas for a Carta for non-venture, and utilizing a media company as a wedge into the expert network spac...
2024-04-0558 min
"Media Empires" | The Business of Newsletters, Podcasts, Creators, and Data AcquisitionAI and Offshore Labor in Service-Based Businesses | Romeen Sheth, MetasysIn today’s episode, Romeen Sheth, CEO of Metasys, joins Erik Torenberg and Sean Linehan to discuss the intersections between Ai and service business, vertical software, and much more.Media Empires is part of the Turpentine podcast network. To learn more: www.turpentine.coWe're hiring across the board at Turpentine and for Erik's personal team on other projects he's incubating. He's hiring a Chief of Staff, EA, Head of Special Projects, Investment Associate, and more. For a list of JDs, check out: eriktorenberg.com.—LINK...
2023-12-1957 min
Founder's Journal3 Frameworks to Hiring Top Talent w/ Romeen ShethEpisode 32: Romeen Sheth (@RomeenSheth) steps in for a guest founder’s journal to share his 3 frameworks related to talent. These simple, but effective frameworks can help any founder hire the right talent to make their organization successful. Not a founder? This also benefits those who are looking for a career change or evaluation by knowing when it's time transition into a new role and how to approach it.Timestamps:(00:52): Intro(01:58): Framework 1 - how to choose where to work(05:28): Framework 2 - develop a personal working guide(08:08): Framework 3...
2023-08-2314 min
Raleigh Williams ExperienceRomeen Sheth on Creating the Best Opportunities for Yourself in Life & Business | S2 EP11Raleigh Williams (https://twitter.com/theraleighwill) dives into a candid chat with Romeen Sheth (https://twitter.com/RomeenSheth) about forging one's destiny, the interplay of intellect and emotion in decision-making, and the true meaning of power in business. They also touch on life after selling a venture and Romeen's golden nuggets of advice. This episode is a masterclass in entrepreneurship and a must-listen for anyone aiming to make their mark in the world of business. Peace!
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About Romeen —
Romeen Sheth is the CEO of Metasys Technologies, a company that collaborates with global firms on talent an...
2023-08-101h 12
Mundane MillionairesRomeen Sheth: The Entrepreneurial Journey (Fear, Motivation and Action)In this episode of Mundane Millionaires, hosts Kevin Henderson and Eric Pacifici sit down with Romeen Sheth, co-CEO of Metasys. Romeen shares his unconventional journey from law school to entrepreneurship, providing a unique perspective on the challenges and rewards of this path. He discusses his decision to forego a traditional legal career, instead leveraging his skills in a more entrepreneurial context.The conversation includes discussion around fears and motivations that come with entrepreneurship. Romeen candidly discusses the sleepless nights and the constant push to move forward, despite the discomfort and paranoia. He emphasizes the importance of self-awareness...
2023-08-091h 06
Not Investment Advice123: Investing in India, VC vs. Bootstrap & Immigrant Hustle w/ Romeen ShethRomeen Sheth joins the NIA boys to discuss Investing in India, VC vs. Bootstrap, Immigrant Hustle and much more Timestamps:(00:00:00) - Intro(00:03:16) - Romeen’s Backstory(00:10:34) - India Deep Dive(00:20:58) - How to think about India(00:25:31) - Framework for Investing in India(00:35:14) - The Indian Consumer(00:45:13) - India and Crypto(00:50:52) - Return on India Breakdown(01:09:04) - VC vs. Bootstrap(01:15:37) - AI Proof BusinessesWhat Is Not Investment Advice?Every week, Jack Butcher, Bilal Zaidi & Trung Phan discuss what they're finding on the edges of the internet + the latest in bus...
2023-08-021h 41
Return on IndiaRomeen Sheth - Reviewing India’s OpportunityThis is Matt Reustle, and for this season's final episode we decided to flip the table and interview Romeen. We talk at a high level about our favorite lessons in the series, some great behind-the-scenes moments across the project, and what Romeen will be monitoring from here. Please enjoy this conversation with Romeen. For the full show notes, transcript, and links to the best content to learn more, check out the episode page here. ----- Return On India is a property of Colossus, LLC. For more episodes of...
2023-03-1643 min
Leveling Up with Eric SiuBootstrapping a $50M+ Business, Growing a Twitter to 120K+ Followers with Romeen ShethThe world has experienced a tremendous amount of change in the past two years and as a result, we are currently in an ongoing state of flux. Making sense of the social landscape we find ourselves in is integral to how we navigate our lives and our careers. It is especially important for anyone involved in investing, marketing, and optimizing new business ventures. We cover some fascinating topics in today's conversation so make sure you tune in to hear it all!TIME-STAMPED SHOW NOTES:
[00:15] Today’s topic: Bootstrapping a $50M+ Business, Growing a Twitter to 120K+ Fo...
2022-04-0741 min
Leveling Up with Eric SiuBootstrapping a $50M+ Business, Growing a Twitter to 120K+ Followers with Romeen ShethThe world has experienced a tremendous amount of change in the past two years and as a result, we are currently in an ongoing state of flux. Making sense of the social landscape we find ourselves in is integral to how we navigate our lives and our careers. It is especially important for anyone involved in investing, marketing, and optimizing new business ventures. Our guest this week is intimately familiar with this dynamic and has dedicated countless hours to learning and applying his acquired knowledge to be an active contributing member of the online community while making incisive business...
2022-04-0739 min
The VITALIZE Podcast: Venture Capital | Startups | Angel InvestingAngel Investing: Romeen Sheth, on Growing and Connecting Authentically as an Operator, Investor, and CreatorJustin Gordon (@justingordon212) talks with Romeen Sheth (@RomeenSheth), who runs $50M bootstrapped business Metasys Technologies, angel invests regularly, and hosts his own podcast, Square One. Romeen is the President of Metasys Technologies, a workforce management advisory firm based in Atlanta. Metasys partners with leading global organizations on the full lifecycle of their talent management strategy. They have been recognized by Inc. 5000 as one of the fastest growing private businesses in the country and work with over 50 leading global organizations today.On his podcast, Square One: Conversations with the Best in Business, he unpacks the journey o...
2022-01-0632 min
ericmckay4 's Listen Later#19 Romeen Sheth - Rethinking Education & Work From First Principles Podcast: Future of Learning & WorkEpisode: #19 Romeen Sheth - Rethinking Education & Work From First PrinciplesPub date: 2021-06-30Get Podcast Transcript →powered by Listen411 - fast audio-to-text and summarizationThis week’s guest is Romeen Sheth. Romeen is President of Metasys, which helps organizations with attracting, engaging, & retaining top talent.
Romeen & I talk about shifts towards flexible work, using first principles & incentive alignment to fix education, angel investing, and the future of learning & work in India.
Follow Spencer Kier on Twitter: twitter.com/SP1NS1R
2021-08-2644 min
The Danny Miranda Podcast#138: Romeen Sheth – 8-Figure CEO on Patience & EmpathyRomeen Sheth is President of Metasys Technologies. He runs an 8-figure revenue bootstrapped business, invests a few million per year in startups, and has his own podcast – Square One. In this conversation, we spoke about debate club, empathy, patience, and what he's learned from taking over a massive company. Romeen's Links Romeen's Twitter – https://twitter.com/RomeenSheth Romeen's Podcast – https://open.spotify.com/show/67XvPFKkeMD9KcRTLcMV0x?si=CUOA51P9Q02ufDG1K5LG-Q&nd=1 Links Mentioned Invest Like The Best with Marc Andressen - https://open.spotify.com/ep...
2021-07-301h 23
Future of Learning & Work#19 Romeen Sheth - Rethinking Education & Work From First PrinciplesThis week’s guest is Romeen Sheth. Romeen is President of Metasys, which helps organizations with attracting, engaging, & retaining top talent.
Romeen & I talk about shifts towards flexible work, using first principles & incentive alignment to fix education, angel investing, and the future of learning & work in India.
Follow Spencer Kier on Twitter: twitter.com/SP1NS1R
2021-06-3044 min
Square One: Conversations with the Best in Business86: Michia Rohrssen, Founder & CEO of ProdigyThe 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.
2021-03-1049 min
Square One: Conversations with the Best in Business85: Jeremy Cai, Founder & CEO of ItalicThis 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 th...
2021-03-0848 min
Square One: Conversations with the Best in Business84: Andrew Yang, Candidate for Mayor of New York CityOver 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...
2021-02-2343 min
Square One: Conversations with the Best in Business83: Chris Bakke, Founder and CEO of LaskieProfessional 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 P...
2021-02-2352 min
Square One: Conversations with the Best in Business82: Tim Ellis, Founder and CEO of Relativity SpaceOn 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 rock...
2021-02-1847 min
Square One: Conversations with the Best in Business81: Julien Smith, Founder and CEO of PracticeCoaching 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...
2021-02-1736 min
Square One: Conversations with the Best in Business80: Hiten Shah, CEO of FYI and Former CEO KissmetricsHow 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 th...
2021-02-0257 min
Square One: Conversations with the Best in Business79: Jonathan Hsu, Co-Founder of Tribe CapitalThis 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 Sl...
2021-01-2935 min
Square One: Conversations with the Best in Business78: Avlok Kohli, CEO of AngelList VentureThis 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...
2021-01-2148 min
Square One: Conversations with the Best in Business77: Nick Donahue, Founder and CEO of AtmosThis 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 solu...
2021-01-1224 min
Square One: Conversations with the Best in Business76: Jason Traff, Founder and President of ShipwellThis 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 rais...
2020-12-1042 min
Square One: Conversations with the Best in Business75: Nikhil Basu Trivedi, Former General Partner at Shasta VenturesThis 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...
2020-12-0338 min
Square One: Conversations with the Best in Business74: 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...
2020-11-171h 05
The Summit PodcastS1E14: Limitless Curiosity and Perseverance | Romeen Sheth (President at Metasys)Romeen is an accomplished young executive who’s achieved substantial success in a short period of time. Today, he is the President of Metasys Technologies, a leading talent firm that works with leading global brands to help them attract, engage, and retain top talent.
In addition to his executive responsibilities, he’s an active early-stage investor having invested in nearly a dozen companies with a goal to invest in many more. Previously, he was a top-ranked management consultant at McKinsey & Company, a leading global management consulting firm.
Romeen received a B.A. from Duke University wher...
2020-11-1157 min
Square One: Conversations with the Best in Business73: Sahil Lavingia, Founder and CEO of GumroadThis 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 ty...
2020-11-1150 min
Square One: Conversations with the Best in Business72: Tom Uebel, Co-Founder and CEO, CommandEWhenever 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...
2020-10-2133 min
Square One: Conversations with the Best in Business71: Shaan Puri, Former CEO of Bebo and Host of My First Million PodcastThis 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. I...
2020-10-1547 min
Square One: Conversations with the Best in Business70: Saahil Goel, Founder and CEO of ShiprocketThis 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...
2020-10-0251 min
Square One: Conversations with the Best in Business69: Michael Mayer, Founder and CEO of BottomlessThis 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...
2020-09-2451 min
Square One: Conversations with the Best in Business68: Ruben Harris, Co-Founder and CEO of Career KarmaSince 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...
2020-09-1858 min
Square One: Conversations with the Best in Business67: Kat Cole, COO and President of FOCUS BrandsThis 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...
2020-09-0951 min
Square One: Conversations with the Best in Business66: Jacob Helberg, Senior Advisor - Stanford University Cyber Policy CenterOver 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...
2020-09-0243 min
Square One: Conversations with the Best in Business65: Turner Novak, General Partner at Gelt VCTik 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 so...
2020-08-1859 min
Square One: Conversations with the Best in Business64: Laura Behrens Wu, Founder and CEO of ShippoSince 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...
2020-08-0543 min
Square One: Conversations with the Best in Business63: Alex MacCaw, Founder and CEO of ClearbitManagement 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 Twit...
2020-07-3050 min
Square One: Conversations with the Best in Business62: Mallun Yen, Founder and GP of Operator CollectiveThe 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 indust...
2020-07-211h 35
Square One: Conversations with the Best in Business61: Ryan Delk, Founder and CEO of PrimerThis 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 princi...
2020-07-1445 min
Square One: Conversations with the Best in Business60: Immad Akhund, Founder and CEO Mercury BankThis 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 on...
2020-07-0839 min
Square One: Conversations with the Best in Business59: 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 an...
2020-06-2355 min
Square One: Conversations with the Best in Business58: Matt Mazzeo, General Partner at CoatueIt’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...
2020-06-1750 min
Square One: Conversations with the Best in Business57: Sean Linehan, Co-Founder and CEO PlacementIn 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.Pl...
2020-06-1152 min
Square One: Conversations with the Best in BusinessE56: Daniel Gross, Founder and CEO of PioneerDaniel 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...
2020-06-0244 min
Square One: Conversations with the Best in Business55: Arjun Sethi, Co-Founder and Managing Partner, Tribe CapitalTribe 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...
2020-05-281h 31
Square One: Conversations with the Best in Business54: Rebecca Kaden, General Partner at Union Square VenturesUnion 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.
2020-05-2734 min
Square One: Conversations with the Best in Business53: Allison Barr Allen, Co-Founder and COO of FastCheckout 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 a...
2020-05-1432 min
Square One: Conversations with the Best in Business52: Mike Slagh, Founder and CEO of ShiftMore 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 wo...
2020-05-1130 min
Square One: Conversations with the Best in Business51: Allison Robinson, Founder and CEO of The Mom ProjectThere’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...
2020-04-2039 min
Square One: Conversations with the Best in Business50: Jason Boehmig, Founder and CEO of IroncladThere'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...
2020-04-1628 min
Square One: Conversations with the Best in Business49: Des Traynor, Co-Founder and Chief Strategy Officer of IntercomAll 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...
2020-04-1256 min
Square One: Conversations with the Best in Business48: Steven Galanis, Founder and CEO of CameoHistorically 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...
2020-04-0742 min
Square One: Conversations with the Best in Business47: Hunter Walk, Co-Founder and Managing Partner Homebrew VenturesThis 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 te...
2020-04-0257 min
Square One: Conversations with the Best in Business46: Jordan Fisher, CEO Standard CognitionAutonomous 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 c...
2020-03-3057 min
Square One: Conversations with the Best in Business45: Vlad Magdalin, Founder and CEO of WebflowNo 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...
2020-03-0543 min
Square One: Conversations with the Best in Business44: Rahul Vohra, Founder and CEO of SuperhumanWorkplace 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...
2020-02-2347 min
Square One: Conversations with the Best in Business43: Sara Mauskopf, Founder and CEO of WinnieChildcare 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 l...
2019-12-0534 min
Square One: Conversations with the Best in Business42: Phin Barnes, General Partner at First Round CapitalThere'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 i...
2019-11-2653 min
Square One: Conversations with the Best in Business41: Julien Smith, Founder of BreatherJulien 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...
2019-10-1851 min
Square One: Conversations with the Best in Business40: Andrew D'Souza, CEO of ClearbancFor 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...
2019-10-0358 min
Square One: Conversations with the Best in Business39: Auren Hoffman, CEO LiveRamp and SafeGraphToday’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.
2019-09-2634 min
Square One: Conversations with the Best in Business38: Elad Gil, Legendary Investor & OperatorElad 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, St...
2019-09-1354 min
Square One: Conversations with the Best in Business37: Mike Knoop, Co-Founder and Chief Product Officer of ZapierIn 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...
2019-09-0443 min
Square One: Conversations with the Best in Business36: Steve Schlafman, Partner at Primary Venture PartnersYou 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 trai...
2019-07-3159 min
Square One: Conversations with the Best in Business35: Paul Arnold, Founder and General Partner of Switch VenturesData 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...
2019-06-2026 min
Square One: Conversations with the Best in Business34: Peter Reinhardt, Founder and CEO of SegmentThe 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 b...
2019-05-1637 min
Square One: Conversations with the Best in Business33: 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 marke...
2019-05-0253 min
Square One: Conversations with the Best in Business32: Brianne Kimmel, Managing Partner at Work Life VenturesJoe 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...
2019-02-2848 min
Square One: Conversations with the Best in Business31: Brynn Putnam, Founder and CEO of MirrorWe 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 v...
2019-02-2127 min
Square One: Conversations with the Best in Business30: Shaan Hathiramani, Founder and CEO of FlockjayThe 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 i...
2019-02-1345 min
Square One: Conversations with the Best in Business29: JD Ross, Co-Founder of OpendoorThe 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. En...
2019-02-0634 min
Square One: Conversations with the Best in Business28: Brent Beshore, Founder and CEO at adventur.esIn 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 wi...
2019-01-2952 min
Square One: Conversations with the Best in Business27: 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 u...
2019-01-2350 min
Square One: Conversations with the Best in Business26: Leo Polovets, General Partner at Susa VenturesAs 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...
2019-01-1043 min
Square One: Conversations with the Best in Business25 Harry Ritter, Founder and CEO of AlmaToday, 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...
2018-11-2340 min
Square One: Conversations with the Best in Business24: Jack Altman, Founder and CEO of LatticeThe 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...
2018-10-3045 min
Square One: Conversations with the Best in Business23: Bradley Tusk, Founder and CEO of Tusk HoldingsIn 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...
2018-10-1849 min
Square One: Conversations with the Best in Business22: Austen Allred, Founder and CEO of Lambda SchoolEducation 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...
2018-10-1038 min
Square One: Conversations with the Best in Business21: Morgan Housel, Partner at Collaborative FundOne 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 Lifec...
2018-08-2648 min
Square One: Conversations with the Best in Business20: Omar Tawakol, CEO of VoiceaOne 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 nat...
2018-07-0235 min
Square One: Conversations with the Best in Business19: Megan Quinn, General Partner at Spark CapitalCoinbase. 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...
2018-05-3145 min
Square One: Conversations with the Best in Business18: Hayley Barna, Co-Founder of BirchBox and General Partner at First Round CapitalAlmost 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 an...
2018-03-2243 min
Square One: Conversations with the Best in Business17: 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 t...
2018-02-1035 min
Square One: Conversations with the Best in Business16: David Tisch, Managing Partner at BoxGroupVery 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 role...
2018-01-2037 min
Square One: Conversations with the Best in Business15: 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...
2017-12-1744 min
Square One: Conversations with the Best in Business14: David Fialkow, Co-Founder and Managing Partner at General Catalyst PartnersSnap. 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 i...
2017-11-1923 min
Square One: Conversations with the Best in Business13: Jason Lemkin, Managing Director at SaaStrVenture 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...
2017-11-0539 min
Square One: Conversations with the Best in Business12: Keith Rabois, General Partner at Khosla VenturesHiring 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...
2017-10-1539 min
Square One: Conversations with the Best in Business11: Jim Feuille, General Partner at Crosslink CapitalThis 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...
2017-10-0942 min
Square One: Conversations with the Best in Business10: Brad Jones, Founding Partner at RedPoint VenturesProduct. 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 e...
2017-06-2456 min
Square One: Conversations with the Best in Business9: David Golden, Managing Partner at Revolution VenturesHigh-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 & Nob...
2017-05-0752 min
Square One: Conversations with the Best in Business8: Ed Colloton, Managing Partner and COO of Bessemer Venture PartnersBessemer 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 Li...
2017-04-2748 min
Square One: Conversations with the Best in Business7: Chris Kelly, Former Chief Privacy Officer of Facebook and Co-Owner of Sacramento KingsThere 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...
2017-04-2354 min
Square One: Conversations with the Best in Business6: Ben Alden, General Counsel of BettermentIt’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 excitin...
2017-04-0849 min
Square One: Conversations with the Best in Business5: Chad Ho, Senior Vice President and General Counsel of HuluChad 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...
2017-03-0442 min
Square One: Conversations with the Best in Business4: Andrew Yang, Founder and CEO of Venture for AmericaAndrew 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...
2017-02-2144 min
Square One: Conversations with the Best in Business3: Patrick Chung, Founder and General Partner at xFundPatrick 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 t...
2017-01-0837 min
Square One: Conversations with the Best in Business2: David Hornik, General Partner at August CapitalDavid 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...
2016-12-1136 min
Square One: Conversations with the Best in Business1: Jim Koch, Founder and Chairman of Boston Beer CompanyJim 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...
2016-11-1235 min