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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 proj…
 
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 th…
 
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 tru…
 
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 a…
 
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…
 
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 Ca…
 
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. Si…
 
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/tec…
 
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 …
 
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 …
 
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 year…
 
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 chan…
 
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, op…
 
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 …
 
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. Amazo…
 
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 e…
 
“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 u…
 
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 ye…
 
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 …
 
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…
 
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 partic…
 
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 mod…
 
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 Karm…
 
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 J…
 
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 intertwi…
 
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…
 
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 w…
 
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…
 
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 c…
 
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, …
 
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 fo…
 
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 wit…
 
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 o…
 
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 …
 
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 re…
 
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 th…
 
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 …
 
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 i…
 
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 w…
 
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…
 
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 a…
 
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 …
 
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 p…
 
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 W…
 
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 perspec…
 
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 w…
 
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 …
 
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 provide…
 
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…
 
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…
 
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