Episodes

Nathan Baschez joins the Deep End to discuss the passion economy, the realities of building a media business, and gets real with Marshall about the realities of embarking on the founder journey as a creator. The two also chat about Every, which Nathan describes as a writer collective for productivity, strategy, leadership, & culture. This conversation with Nathan blends a few different threads that we've covered on The Deep End. Nathan's background as a prolific writer & podcaster makes this a natural extension of the conversation that we covered when discussing Creator-Operators with Josh Kaplan two weeks ago. We chat about the wavering stability of media companies and the obvious upside of the substack economy to creators. We ruminate on questions like “Should writers try to become stars in their own right?” and “What did early millennial-centric media businesses get wrong?” while examining how ambitious people often are replicating their behavior based on the models that have p…

Joining the Deep End is Doug Ludlow, CEO of Mainstreet. Today's conversation is about the unbundling and re-bundling of the smart bank and how the 35 million small businesses in the US can benefit from aggregating their business identity data in one place. We talk about helping small businesses navigate PPP loans during COVID, discuss how startups can earn tax credits easily for things like research & development and other ways that  Mainstreet can help restore America's economy coming out of the pandemic. Doug was a particularly fascinating guest because he has spent his life between two worlds. There's the tech world, where he's been a senior employee at Google, AOL, and other iconic tech companies, and then there's the world of his upbringing: he grew up in a small, rural USA town t where farmers have been seeing  their land get consolidated and sold off. His unique perspective led us to chat about the brain drain among US heartland cities and how the rise of remote work might …

At On Deck, we believe that startups are the building blocks of a better future. Startups drive global economic growth by creating jobs, improving quality of life, and making meaningful progress to solving society's biggest problems. We also believe that the the biggest constraint on startup creation is the number of founders - for each person starting a company today, there are hundreds more sitting on the sidelines. This is an enormous waste of human potential. That's why we are excited to announce ODX - a $100 million community-backed fund to put the next generation of founders in business. ODX backs founders with a check for $125,000 and unlimited access to the On Deck network, which includes thousands of companies, founders, operators, and investors that builders can tap into for talent, capital, and distribution. Many of those investors & operators are also participants in the community-backed fund, meaning that they are personally incentivized to help ODX participants succeed…

Joining Marshall in the Deep End is Sara Du - cofounder & CEO of Alloy Automation, a no-code tool for automating e-commerce stores. The conversation begins by discussing how the line between commerce and e-commerce is blurring as e-commerce penetration continues to accelerate across the consumer economy. This trend was certainly accelerated by the pandemic, but Sara notes that Black Friday shopping patterns and other indicators suggest that such a shift was inevitable anyways. The discussion then moved to the power of no-code tools, and their potential applications to helping unlock value for small businesses without engineering teams. Sara thinks that Alloy can be for commerce what Zapier has been for tech. Finally, we discussed the implications of automation itself. Does it replace jobs or augment current ones?

Karthik Puvvada (known by his friends and online as "KP") is the Program Director for On Deck No-Code and is also a leader of the "build in public" movement that is taking the internet by storm. Today's conversation takes place at the intersection of those two tech trends. When KP thinks about building in public, he encourages his audience to use content as a lighthouse to attract other people to your circle. These content pieces help to signal that you're serious about a certain niche and help prevent you from being washed away by the "Internet Content Stream." Stories are how you stand out in a crowded digital world. KP's stories have elevated his no-code platform. He's excited about how the builders of today don't need coding skills to create tools because they can use drag & drop solutions. We talk about projects in the no-code space that are fresh and exciting, as well as classics that have proven real staying power. KP's enthusiasm, humility, and charisma all come oozing out …

Josh Kaplan was an early employee at Morning Brew and was a product manager during their meteoric rise as a media company. Now, he’s taken what he has learned as an operator in a creative space and applied it to his role as co-founder and CEO of Smooth Ops to help content creators scale their businesses. Today’s conversation is about the deeply challenging logistics involved in the creator economy. Josh contends that most creators find themselves thinking relatively short-term. While it’s important to focus on producing great content, it’s also crucial to plan for the future—not just the next podcast episode or newsletter. Creators need operators as partners to help them think about and build for the long term, even as they focus on the next project at hand. This core theme led us in all sorts of interesting directions. We discuss the competition for talented producers on the frontlines of creative markets, how the flow of social relationships has changed, and how to create optiona…

Bored Elon Musk (one of Twitter's largest pseudonyms with 1.7 million followers) joins us to discuss the nature of pseudonyms and his investment activity. We also chat about the metaverse, the pseudonymous tech stack, the future of deep fakes, and much more. Pseudonyms are interesting because they are inherently meritocratic. Bias isn't possible because nobody knows who you really are. As the internet becomes more crypto-native and employment becomes more fluid, pseudonyms will only continue to rise in popularity. Already, DAOs are full of contributors that use pseudonyms. It's worth noting that pseudonymity is not anonymity. A pseudonym can build reputation that persists through interactions. Bored Elon is trying to make sure that as one of the first major pseudonyms, he sets the right example with his online reputation. Besides posting memes or tweeting fake startup ideas, Bored Elon is spending a lot of time investing in real companies with the bored fund. Many founders are hap…

This week's guest on The Deep End is Dr. Emily Anhalt (@dremilyanhalt on Twitter). Dr. Anhalt is a psychologist, emotional fitness consultant, and the Co-Founder and Chief Clinical Officer of Coa, which describes itself as building a gym for your mental health. Today's conversation is about how to train for emotional fitness. Just like trainers at a traditional gym might rotate clients between a leg day, chest day, and shoulder day, Dr. Anhalt and her colleagues have developed classes to train different traits of emotional fitness like resilience, empathy, and self-awareness. In addition to discussing what exactly goes into performing the equivalent of an emotional push-up, we dive into how the pandemic has influenced the mental health landscape, analyze the stigma around seeking help, and compare & contrast in-person therapy with virtual options.

Cooper Turley leads a handful of online communities known as DAOs. "DAO" is an acronym that stands for a decentralized autonomous organization. In more colloquial terms, a DAO is an internet community with a shared cap table and bank account. They represent humanity's newest structure for cooperative decision making. Cooper joined us for a live episode last week to help explain why DAOs are exploding in popularity. In our discussion, he explained their governance structures, described the different types of DAOs, made some predictions for the future,, and answered some wide-ranging questions from our live audience. DAOs are a powerful new mechanism for coordinating humans at scale. If they work as intended, we could be seeing the rise of a new way of organizing people that might last for centuries. We hope you enjoy!

It's a new season of the Deep End and we're moving to two episodes per week (Mondays + Wednesdays)! We lay the groundwork for all of our upcoming episodes by discussing the nature of the open-source web. Our guest, Cal.com Co-CEO Peer Richelsen, views the internet as a democratic, transparent, and open technology that is undergoing a renaissance. Open-source software development was the spiritual precursor to 2021's web 3 boom. Tinkerers like Peer are ecstatic that technologists are returning to the very fundamentals of the web that made it so inclusive and exciting in the early 2000s. In this episode, Peer explains how the Internet can finally return to its decentralized roots because of incentive structures that have developed over the last few years. We also dive into several fun other topics, including how to pick the right web domain, how to build a company with two CEOs, and what the differences in cultures of compensation transparency are between the US and Germany.

Dean Hollis Robbins wears many hats: Administrator, teacher, scholar of black sonnets... but she's also an expert on expertise itself. Today's conversation is about frameworks for organizing knowledge. Dr. Robbins argues that our modern society suffers from mismanaged "self-secretarying" - most of us receive no formal training in how to process & sort the huge amounts of information that we have to process every day. She also straddles the line between higher education and tech. Her involvement in both communities helps her understand how these two different worlds might both be able to learn from each other. This interdisciplinary background of hers made this conversation a fascinating examination of the interplay between breadth and depth.

Patrick Rivera (Product Engineer at Mirror) has a front seat on the edge of the crypto revolution. He details the evolution of the internet from Web 1.0 to 2.0 to 3.0, discusses the crypto-native creator economy, paints a picture of the current crypto landscape (and challenges), and provides some predictions for the future.

Flo Crivello (CEO of Teamflow) believes that a new way of working calls for an entirely new set of tools. In this conversation, we explore how employers can curate a new kind of space that looks virtual, but feels intimate and collaborative in the same way a traditional office does. Our wide-ranging conversation covers text-based productivity vs. video-based work, the entrance of Facebook into the remote work space, the implications of visa immigrations in a borderless world, and much more.

We sit down with Marc Lore, a serial entrepreneur and self-described "moonshot seeker." He has successfully founded and sold three companies, including Jet.com, which sold to Walmart in 2016 for $3.3 billion. Now, he's building a mission-driven city called, "Telosa," which comes from an Aristotle-coined word "Telos," meaning "a higher purpose.”

We sit down with Gaby Goldberg, investor at Bessemer and explorer of the metaverse. Also joining us is Shriya Nevatia, program director of On Deck Catalyst.

We sit down with Delian Asparouhov, co-founder of Varda Space Industries. He explains why Varda’s mission statement is to “expand the economic bounds of humanity” and how its success will do for space what the gold rush did for California.

We sit down with Sam and Andrew who, since meeting during On Deck, have gone on to co-found a startup called Levels. Their goal is nothing short of changing the way the world interacts with food through the creation of a whole new product category centered around metabolic health.

We sit down with Kyla Scanlon, a content creator and program partner at On Deck Investing— a fellowship for investors who want to deepen their knowledge of public markets, understand investor psychology, and accumulate practical tools for long-term wealth creation.

We sit down with Candice Ammori, Program Director of the On Deck Climate Tech fellowship — a 10-week program for startup and climate experts looking to start, join, invest in, and advise climate tech companies.

We sit down with Fadeke Adegbuyi, self-described “tech optimist” and creator of Cybernaut — a newsletter that explores the wide-ranging and sometimes “weird” communities and cultures of the Internet.

We sit down with Packy McCormick, writer of the popular Not Boring newsletter and startup investor via Not Boring Capital. The following conversation was recorded live on the internet in front of an audience of On Deck community members and fans of the podcast.

We sit down with Rebecca Kaden, a Managing Partner at Union Square Ventures to discuss thesis-driven investing. The following conversation was recorded live during the recent On Deck New York City drop.

We talk with Web Smith, an expert on consumer brands and ecommerce and the founder of 2PM, an online resource that analyzes the intersection of media and commerce.

We talk with Jarrod Dicker, investor at the Chernin Group and former Washington Post executive, about how modern creators are driving the development of new applications and ushering us into a new era—the decentralized web, also referred to as web3.