Episodes

Joining us in The Deep End today is Tory Reiss. Tory is the CEO and co-Founder of Equi, an alternative investment hedge fund. Tory previously co-founded Archblock, a decentralized alternatives marketplace, and Harvest Money, an AI-driven debt management platform. We’re taking a quick break from our series on starting companies, to take a quick dive into the world of fintech. Our conversation with Tory today centers around how you can take control of your financial destiny and Tory’s journey from a Google Docs to starting Equi.

Joining us in The Deep End is Ansel Parikh. Ansel is the co-founder of Finch, an API for Employment Systems that democratizes access to the infrastructure that underpins the employment sector. Finch recently raised a $40M Series B. Before Finch, Ansel was a late-stage investor at Kleiner Perkins and Bond. Ansel shares how they landed on the name for Finch, why US employment regulations are so complex, how Finch’s infrastructure helps companies get to market and why you should fail as quickly as possible as a founder.

Gina Gotthilf is the co-founder and COO at Latitud, a platform helping build the next generation of iconic tech startups in Latin America through products, a dedicated fellowship and fund. Gina met her co-founder, Brian Requart, through On Deck. Before Latitud, Gina was the VP of Marketing and Growth at Duoloingo, helping scale the company from 3 to 200 million users, and worked on the Mike Bloomberg presidential campaign. Continuing with our series on the meta-problem of helping people start companies, we talk to Gina about the bottlenecks to starting companies outside the United States.

Joining us in The Deep End today is Sophie Alcorn. Sophie is the founder of Alcorn, a Silicon Valley immigration law firm that helps tech talent immigrate to the US. She is also the host of the podcast Immigration Law for Tech Startups and author the TechCrunch weekly immigration advice column “Dear Sophie.” Continuing with our series on the meta-problem of helping people start more companies, we talk to Sophie to understand why immigration is a bottleneck to company creation, and what founders, investors, and policy-makers can do about it.

On The Deep End today, we welcome Sasha Orloff, the Founder and CEO of [Puzzle](http://puzzle.io), a modern accounting software package for startups that recently raised $15 million in series A. Sasha joins us to discuss the use of accounting as a powerful decision-making tool and the creation of infrastructure to start and scale businesses, as part of our series on meta-problems to help founders start more companies. Despite advances in financial technology, Sasha believes that core accounting software remains outdated and does not take advantage of modern capabilities. He suggests that accounting could be a competitive advantage for businesses if it were reimagined as a tool for data-driven decision-making, empowering founders to build better businesses. During the episode, Sasha identifies three key areas that founders should focus on when fundraising: telling a compelling story, taking the process seriously, and planning for success: Founders must have a strong answer for what s…

Joining me us the Deep End today is Minn Kim. Minn spent a few years as an investor at Ridge, Bloomberg Beta and On Deck, backing founders as early as possible and is now building Plymouth to help extraordinary talent immigrate to the US. In this conversation we go deep into Minn’s core belief – that technology enables step changes in human agency. We discuss navigating the idea maze, picking who to start a company with, why immigration is key to innovation and so much more.

Last week in The Deep End we spoke with David Booth, CEO of On Deck. Today we're continuing our mini-series on the meta problem of how to help more people start more companies by re-publishing an episode of the Solarpunk podcadst with Erik Torenberg, co-founder and Chairman of On Deck. Erik joins Lucas Bagno and Ian Cinnamon discuss why startups are the most effective organizations for solving our biggest problems, how governments and startups need to work together, not against each other, the rising importance of story-telling and much more.

David Booth is the CEO of On Deck, a curated community designed to increase your odds of building a successful venture-backed company. In this conversation, we discuss why On Deck is doubling down on IRL programming, why he believes venture-backed founders need to be deeply connected to the Bay Area, why now is the best time to start a company, and how startups help combat stagnation.

Vivian Chen is the CEO & Founder of Heyo, a bite-sized pitch platform for professional success. Before starting Heyo,Vivian was an operator who built products across categories from high-growth startups to global enterprises. Vivian is on a mission to build the future of work. Heyo enables users to build profiles online short-form content and video, offering a new way to tell your professional story. In this conversation, we discuss Vivian’s founder journey, how she maintained her vision in the face of setbacks, rapidly shifting market conditions, and the need to pivot in the face of experience. We also cover how short-form video can help anyone stand-out in crowded professionals spaces and offer new opportunities to the previously overlooked. In this conversation, we discuss Joseph’s founder journey in education over the last ten years, why government inefficiencies present such an interesting – but hard – problem to solve, and how a platform like Odyssey has the potential to addr…

Ani Pai is an investment partner at Dragonfly, where he focuses on highly technical Web3 projects in emerging markets. Ani believes that progress happens on the frontier. Whether it be outer space, the mind/body, and the oceans. He’s focused on using crypto to explore these frontiers and eventually merging crypto networks with analog industries in order to shepherd the next billions users into web3. We discuss the state of the crypto industry in the wake of FTX’s implosion, why he believes the next generation of founders will need to be “polymathic in their interests and skillsets, and whether web3’s promise will be fulfilled in the United States or emerging markets, or even a network state/new country. This episode is for anyone interested in how the marriage of crypto bits with the world of atoms could define the next era of tech. Learn more about Dragonfly here: https://www.dragonfly.xyz/

Lauren Self is the founder of Roots Homes, a platform that helps put the dream of homeownership within reach by allowing prospective buyers to effectively pay rent while building equity in their home with fractional ownership. In this conversation, we discuss her founder journey and life experiences that motivate her to build in this space, why the dream of owning a home feels increasingly out of reach, why she believes her model is superior to perma-renting, and how the concept of fractional ownership can expand to use-cases beyond the real estate market. This episode is for anyone interested in how new business models can open up previously gated opportunities to new generations. Learn more about Roots here: https://www.roots.homes/

Madison Campbell is Co-Founder and CEO of Leda Health, which provides aftercare for sexual assault survivors. Leda Health approaches its space through a survivor-focused lens, developing self-administered DNA collection and testing, while also connecting survivors with professionals and resources. In this conversation, we discuss her founder journey since leaving school to pursue a startup, fundraising in a sensitive product category, and how the nimble approaches required to found and build an early startup can be the best means of addressing real-world problems. This episode is for anyone interested in the intersection of healthcare, technology, and seemingly intractable challenges. Learn more about Leda Health at: https://www.leda.co/

Joseph Connor is the CEO & founder of Odyssey, a platform that helps families access state microgrants for K-12 education. Prior to starting Odyssey, Joseph was a former teacher, school founder, and attorney. Joseph and his team at Odyssey are on a mission to empower everyday parents by enabling access to public education dollars. Odyssey’s technology provides states with a turnkey platform to manage microgrant programs. A growing number of policymakers view microgrant programs as a tool to bridge equity gaps between families in under-resourced communities and their more affluent peers. Yet implementation has been challenging and these funds have not achieved the desired impact or reached parents’ pockets at scale. Odyssey is partnering with states to help smooth implementation, and ensure all eligible families are able to benefit. In this conversation, we discuss Joseph’s founder journey in education over the last ten years, why government inefficiencies present such an interesti…

Andrew Rea is an angel investor and operator, who recently started and organized New York Tech Week. He leads go-to-market at Capital (formerly Party Round) and has invested in over 20 startups, including Motion and Cococart. Before he was at Capital, Andrew was vital in building the community at the On Deck Angels fellowship. Andrew also has founder experience, having co-founded an EV startup, raised $1M, and sold to PE within 2 years. In this conversation, we discuss how New York Tech Week came about, how to think about the advantages of the New York tech ecosystem compared to other tech hubs, and what Andrew is hearing from elite founders about gaining traction and building companies in the current climate. This episode is for anyone interested in better understanding the tech scene hubs and industry events and what it takes to pull off a tech week in less than two months.

Erik Torenberg (@eriktorenberg), co-founder and Executive Chairman of On Deck join Lucas Bagno and Ian Cinnamon on this episode of Solarpunk. Village Global’s Solarpunk is a podcast series about technology, space, and defense. Takeaways: - Startups are the most effective organizations for solving our biggest problems. - Startups disproportionately contribute to economic growth. - Governments and startups need to work together, not against each other. - China has the GDP per capita of Mexico but they have power because of how big their population is. - Increasing population should be an aim of the US government. - Humans are a naturally technological species and the only way out of our current problems is through technology, not without it. - People in Silicon Valley need to invest in storytelling and capturing hearts and minds. They have a new appreciation for how important politics is. - Ideas from Silicon Valley are being exported around the world —among them are giving without aski…

Lawson Baker is the Founder of RARA, a social curation protocol for NFTs that revolutionizes how creators benefit from sharing their art, and how curators interact with and gain value from interacting with artists’ work. Our discussion centers around how web3 will forever change the dynamic between creators and curators. “Likes” and “heart” buttons are remnants of web2 — RARA creates tools to move away from centralized curation to decentralized curation, where fans can be rewarded for recognizing popular or viral art early. Users are tired of doing free labor for social media platforms. With RARA social, creators gain value from how much users interact with their art, and fans gain curation tokens for recognizing popular art early. The name of the company — Ra Ra — refers to a cheer, and in that vein, the protocol is powered by web3 reactions. Users burn reactions on NFTs that they like and receive curation tokens in exchange. The more that other people react to that NFT, the more…

Rehan is the Founder and CEO of Chptr, a startup fixing the way the world remembers people who have passed away. Prior to creating Chptr, he had a long career in music, founding the “Life is Beautiful” festival, and led marketing teams at high-profile Las Vegas hotels. Rehan and his team at Chptr are vying for the memorialization space, which up until now has been owned by legacy media obit pages and Facebook timelines. The broader death tech industry is estimated to reach over $128B this year and steadily growing, especially in the wake of the COVID-19 pandemic. Rehan’s soulful vision for Chptr is a model for community building around death, based on user behaviors trained by precursor social networks built to chronicle lives. In this conversation, we discuss how Chptr can reimagine how we memorialize loved ones, the maturation of the social media space, and how On Deck helped him on his founder’s journey. This episode is for anyone interested in the future of social networks, id…

Julian Weisser is the co-founder of On Deck, partner at our Founders and Angels programs, and investor at Other Ventures. He is a prolific startup investor and has backed over 100 companies ranging from asteroid mining to dog longevity and decentralized museums. He’s often one of the first angels that founders seek out for guidance on how to construct their fundraise. Our discussion today covers how Julian started investing with just $1k in multiple companies, while building his investment philosophy and portfolio track record. We debate about the new evolution of how founders start companies, what is momentum capital in startups, and why Julian feels like now is the best time to start a company. We also get into details from Julian’s experience working with founders and how to align on the fundamentals when looking for a co-founder. Hosted by Marshall Kosloff.

Emmanuel Straschnov is the Co-CEO and Founder of Bubble, an online tool to build web applications without code. Our discussion is about the state of No Code: what it is, where it came from, and where it's going. The pandemic saw a huge growth of interest in No Code in mid-to-late 2020 as people everywhere began looking for cheap and fast ways they could start building from their own homes. We also talk about how and why Emmanuel chose to bootstrap when he was starting Bubble, and why a lot of Bubble users choose to bootstrap their own companies too: with the ability to build a web app cheaply and quickly at your fingertips, there isn’t as much of a need for fundraising or having a technical co-founder as there was before. With No Code tools like Bubble, will technical founders, or even coding itself, eventually become obsolete? This episode is for anyone interested in starting their own venture, or anyone, regardless of industry, who is looking for No Code tools to build their f…

JD Ross (@justindross) and Justin Blau (@3LAU), co-founders of Royal, join Erik Torenberg and co-host Ian Cinnamon for this episode of Venture Stories web3 series. Takeaways: - Royal stems from their vision to invest in talent early on. - Streaming increased by 60-70x in about 5 years from 2015 on. - The barrier to entry for artists is much lower — they no longer need a studio, they just need a laptop. - Royal is trying to enable the fan-artist relationship to be more of a partnership. - When fans own a part of an artist’s song, they are tied for life. - Justin has sold a ton of tickets in his career but he has zero idea of who those fans are and doesn’t have the ability to contact them. The data layer built into Royal helps artists connect with their fans.

Eugenia Kuyda is the founder and CEO of Replika, an AI companion company. Our conversation today centers around the different use-cases of AI, from task-oriented chatbots to emotionally-supportive AI companionship. We delve into the current state of conversational tech, including how chatbots can become good listeners, and why Replika used a mixture of scripted retrievals and generative AI models for their product. We also talk about the differences between an AI companion, virtual assistant, and chatbots. We also discussed the past and future of AI and chatbots. Eugenia explains why task-oriented chatbots like a restaurant booking bot she had worked on previously didn’t catch on in the past, and the future she envisions where you can have an AI co-pilot of your life, like Jarvis from Iron Man, and how this can interact with her conception of the metaverse which she calls the “embodied internet”. This is a great episode for anyone who’s interested in possible futures of how AI can …

Today, we’re syndicating an episode from the Village Global podcast hosted by On Deck co-CEO Erik Torenberg. The guest on the show is Mike Shebat - CEO & Co-founder of Traba and a member of Forbes 30 Under 30. Mike participated in the 8th cohort of our On Deck Founder fellowship. He and the team at traba recently closed a $20M to match contractors with events and warehouse work. He met one of his co-founders, Akshay, through On Deck. Prior to starting Traba, Mike was a founding member of the Uber Eats team. For more stories like Mike’s, check out beondeck.com/stories

A year ago, we launched The Deep End with Balaji Srinivasan as one of our first three guests. In the episode, he discussed the impending arrival of The Network State. Flash forward to this Monday on the fourth of July when Balaji released his book “The Network State: How to Start a New Country.” In a single sentence, a network state is a highly aligned online community with a capacity for collective action that crowdfunds territory around the world and eventually gains diplomatic recognition from pre-existing states. In this episode, Saagar Enjeti (another past guest of the show) and Marshall revisit some of the themes from last year’s Deep End episode and try to better understand Balaji’s frameworks for understanding the futures of tech and nation states. Let’s dive in to this syndicated episode from The Realignment, Marshall's other podcast.

Mark Switaj is co-founder & CEO of Roundtrip Health. Roundtrip is driving better health by providing a full suite of non emergent transportation options to patients in different care settings across the country. After exploring the India and health tech market in India last week, we wanted to revisit  healthcare in the US.  Today’s conversation is about social determinants of health. Social determinants of health (SDOH) are the conditions in the environments where people are born, live, learn, work, play, worship, and age that affect a wide range of health, functioning, and quality-of-life outcomes and risks. Roundtrip specifically is focusing on transportation - 4 million people miss appointments every year because of a transportation barrier. But Mark is able to speak to how organizations more broadly must lean on data insights in order to improve health outcomes. We also talk about how the pandemic has affected the domestic health tech and telehealth landscapes. Mark’s comments…