The Deep End by ODF

Cal.com CEO Bailey Pumfleet turned a side project into one of the most ambitious infrastructure companies ever.His mission: powering a billion connections by 2031Rather than just another Calendly alternative, they're building the "Stripe for Time" - scheduling infrastructure that powers everything from doctor's appointments to refugee services.We get into:[3:56] How startups get open source wrong[10:46] Launching the v0 of Cal (called Calendso)[24:32] Why open source is crucial for infrastructure companies[36:30] The journey from MVP to enterprise-grade platform[39:29] Building trust through radical transparency[46:46] How their "longevity guarantee" wins enterprise deals[47:15] Running a fully remote global team[53:00] Handling compliance and security at scaleThis is a must-watch for anyone building infrastructure, open source, or startups in general..Enjoy!Links mentioned:ODF: explore starting a startup in SF and figure out co-founders, customers, and more at https://joinodf.comStampList: browse breakout companies with a track record of sponsoring visas for exceptional talent at https://landing.club/stamplisthttps://cal.comhttps://x.com/BaileyPumfleethttps://x.com/peer_rich (Bailey's co-founder)https://x.com/julianweisserThe Deep End is available on YouTube and other podcasting platforms:https://www.youtube.com/watch?v=V2Pripb427EApple: https://podcasts.apple.com/us/podcast/the-deep-end-by-odf/id1568752165Spotify: https://open.spotify.com/show/4TWOlf80GM1Pml8fGUO8KK

Eoghan McCabe is the CEO and co-founder of IntercomThis was an incredible talk recorded live during the ODF22 cohort. Thanks again to Intercom for hosting.10 important ideas (and timestamps) from this conversation:1/ Innocence and Naivety Can Be a Superpower7:58 - “There was a phenomenal amount of naivety that allowed people to do things that were kind of like conventionally the wrong thing to do.”2/ Be Contrarian, but Not Recklessly So10:05 - “If you talk to 100 funds right now and you can’t raise money, change the damn idea.”3/ In-Person Work is Better11:55 - “In person is better. And I think that the people who promote remote working are lazy and antisocial.”4/ Find Your True Passion—or You'll Fail17:55 - “Please follow your passion. Please do the thing that you love.”5/ Great Companies Ride Multiple Waves21:23 - “Great companies are built on successive waves… secular movements. They either create them themselves or they jump on ones that have started already.”6/ Hard Work is Under Attack—But It's Essential23:37 - “Most likely you’re going to want to need to work seven days a week and 12 hours a day to get your thing off the ground.”7/ Extreme Homogeneity Early On Beats Diversity25:03 - “In early-stage startups, you want extreme homogeneity. You want people who believe what you believe.”8/ Customer Intimacy Over Everything26:29 - “They’ll obsess about talking to customers… getting inside not just their heads but their hearts.”9/ Early Failure and Rejection Strengthens You29:08 - “The things that bruise our egos the most tend to eviscerate the parts of our ego that were making us so fragile in the first place.”10/ Hiring Brilliant People is More Important than the Idea41:51 - “The people who put that team together had an eye for that X factor.”--If you're exploring starting a company apply for ODF - our 23rd cohort kicks off November 8th in San Francisco

Today we’re chatting with Mo El Mahallawy, CTO and co-founder of Shepherd.Shepherd is all in one commercial insurance platform focused on high hazard industries. The company is on an absolute tear and this month they announced a $13.5M series A.Mo and I decided to sit down and record a conversation because the journey of Shepherd will resonate with many potential founders who are try to find those two key missing pieces: who might I start a company with and what might we build together?Right as the world was shutting down due to COVID, Mo joined ODF3 where he met one of his co-founders at Shepherd — Justin Levine. Mo and Justin soon embarked on a journey to determine what they could build together that had potential to solve a real customer problem.After pivoting through several ideas across a variety of sectors, they honed in on an area where one of them had a unique insight — construction insurance.This is an instructive story about how to find co-founders and how to build a great business together. Enjoy!Are you exploring starting a company? We’ve got a program for that!ODF has helped 1k companies like Shepherd (ODF3) find their co-founders, get started and go on to raise over $2B. Applications for our IRL cohorts in San Francisco are now open. Learn more and apply at beondeck.comMo on X/Twitter and his company Shepherd.beondeck.comOn Deck on X/TwitterJulian on X/Twitter and blogPodcast episode archive and show notes

Today’s conversation is rare but vital — we spend much of our time talking about the challenges around shutting down companies. While I spend most of my time writing about how to build towards success, the stark reality is that most companies fail. Shutting down your company is incredibly painful but it’s particularly lonely — you often feel like you have limited support and guidance.That’s why Stevie and I felt it was so important to record this episode. We hope this episode is a resource to every founder in the years ahead that makes the decision that it’s time to move on. It’s packed with personal stories from Stevie, tested tactics, and best practices.We also spend some time talking about startups, identity, and the long arc of ambition. Contrary to what you might expect, I found this to be an inspiring and entertaining conversation — I think you will as well.Are you exploring starting a company? We’ve got a program for that!ODF has helped 1k companies get started and go on to raise over $2B. Applications for our IRL cohorts in San Francisco are now open. Learn more and apply at beondeck.comStevie on X/Twitter and her newsletter Highly Regulatedbeondeck.comOn Deck on X/TwitterJulian on X/Twitter and blogPodcast episode archive and show notes

ODF is thrilled to announce its partnership with Puzzle — all ODF participants and alumni now save hundreds of dollars, To learn more go here.--Are you exploring starting a company? We’ve got a program for that!ODF has helped 1k companies—like Puzzle which was ODF8—get started and go on to raise over $2B. Applications for our IRL cohorts in San Francisco are now open. Learn more and apply at beondeck.compuzzle.ioSasha on X/Twitterbeondeck.comOn Deck on X/TwitterPodcast episode archive and show notesFor this episode of the Deep End, Sasha dropped by On Deck co-founder Julian Weisser's house in SF to talk about why he decided to decade his next decade to building better accounting software for startups.Sasha realized that building Puzzle was essential for startups to have the best chance at thriving in an increasingly complex world. Puzzle puts accounting on autopilot and enables founders to be able to zoom in on any area of their business, model out scenarios, and plan for the future. It also makes the diligence process during finance and acquisitions go smoother.

Are you exploring starting a company? We’ve got a program for that!ODF has helped 1k companies—like Respell which was ODF17—get started and go on to raise over $2B. Applications for our 20th cohort in San Francisco are now . Learn more and apply at beondeck.comrespell.aiMatt on X/Twitterbeondeck.comOn Deck on X/TwitterPodcast episode archive and show notesFor this episode of the Deep End, Matt Rastovac dropped by On Deck co-founder Julian Weisser's house in SF to talk all things AI and his experience as a second-time founder.With his new company Respell, Matt is building AI-powered workflows and agents to assist on tasks enabling individuals and teams can be more effective than ever before. During our conversation Matt shares how he thought through building the first version of Respell, how to educate potential customers about breakthrough technology, and what he’s learned about sales.Prior to Respell, Matt was the co-founder and CTO of Atmos a vertically integrated solution for building a custom home. Matt shares what he learned at his first company, how he’s transitioned into the CEO role at his second one, his unique and compelling method of hiring and evaluating talent, and much more.

Earlier this week Celine Halioua (ODF2), founder and CEO of Loyal — a dog longevity biotech startup — announced something truly groundbreaking.Loyal (ODF2) has earned what they believe to be the FDA’s first-ever formal acceptance that a drug can be developed and approved for lifespan extension. As Celine says in her announcement; “I started Loyal 4 years ago with the explicit goal to get the first drug FDA approved for lifespan extension itself - no disease, just healthy, longer"..."We can't start selling the drug yet - we need to complete the safety and manufacturing technical sections - but this represents the lions share of the 'existential risk' of both the drug program, and of Loyal AKA - we are doing it!!!”Laura Deming is a longevity biotech investor with an incredible batting average. 5 of 18 startups she’s backed so far have gone public. She was the first investor in Loyal and had this to say:"This just dropped - the most important milestone in the history of longevity biotech. put simply, this is the FDA’s first-ever formal acceptance that a drug can be developed and approved to extend lifespan. the longevity field is evolving quickly. No one I know in the field would have said this was possible 5 years ago. Celine got it done in 4. It’s a massive win for both biotech founders and regulators, in establishing a pathway by which drugs (initially for dogs) can get approved for lifespan"You’re about to listen to an archival interview with Celine just one and a half years into starting Loyal which is now 4 years old. It’s an incredible conversation with interviewer Marshall Kosloff and shows just how much can be accomplished in a few short years.Congrats to Celine and the entire Loyal team on what is truly an unparalleled milestone.Are you exploring starting a company we’ve got a program for that?ODF has helped 1k companies like Loyal which was ODF2 get started and go on to raise over $2B. Applications for our 20th cohort in San Francisco are now . Learn more and apply at beondeck.comloyalfordogs.comCeline's personal websiteCeline on X/Twitterbeondeck.comOn Deck on X/Twitterpodcast episode archive and show notes

Joining me in the deep end is US Navy veteran Mike Slagh — founder of Shift — an organization that has built the most significant bridge between the Department of Defense and the startup ecosystem.Defense Tech is a big deal. We’re just now starting to see it be thought of as a more feasible sector to build startups. Mike might be one of the best people in the world to learn about opportunities to build tech and services that support America and our allies.Before co-founding Shift, Mike felt a calling to serve and joined the United States Naval Academy and was a bomb disposal officer for half a decade.Mike’s first experiences with business go all the way back to when he was a kid helping his grandma Betty run her toy store. As a teenager he became an eBay power seller to generate an additional income stream for their business.In just under 10 days Mike is hosting the Defense Venture Summit, convening founders, operators, over 100 VC funds, and members of the US Military. It’s likely sold out as of publication. But if you are interested feel free to DM Mike on Twitter to see if you can be included.In this episode, Mike and I discuss opportunities in defense tech, a history of the sector, what he’s learned building a premier talent org, hiring veterans, and much more.Are you exploring starting a company we’ve got a program for that.ODF has helped 1k companies get started and go on to raise over $2B.I’m actually recording this podcast intro at our partner Carta’s office as they are hosting us during the 19th cohort of ODF happening right now. The energy is incredible — I’m excited to see what this cohort builds.We’ve just started reviewing applications for our 20th cohort taking place in San Francisco in late January. Learn more and apply at beondeck.comWithout further ado, here’s my conversation with Mike Slagh

Are you exploring starting a company? We’ve got a program for that.ODF has helped 1k companies get started and go on to raise over $2B. Applications for our 19th cohort in San Francisco are due this week. Learn more and apply at beondeck.com--Joining me in the deep end is Max Greenwald — co-founder of Warmly a startup that helps businesses turn warm leads into sales. The company recently announced their series A.I’ve known Max for years and watched the Warmly journey unfold — Max even met his co-founder Alan through ODF.Warmly’s path has not been a straight line. This conversation with Max is candid. He shares the mistakes and lessons learned on the journey towards building a product that customers love.This might be one of the most useful episodes we’ve recorded on the deep end in terms of giving actionable guidance for founders.In this episode, we discuss how to communicate changes in direction to investors and teammates, how to avoid the sunk cost fallacy, how to work with initial design partners, and much more.

Joining me in the deep end is Elaine Zelby — co-founder of Tofu (https://www.tofuhq.com/) — a powerful generative AI platform that enables marketing teams to repurpose their content and run more successful campaigns. Tofu recently announced their $5M seed round led by Index Ventures.We’ve known Elaine for years — first as a friend, then as a participant in ODF2, then as an investor in On Deck during her time as a VC at SignalFire. She’s the first person we refer founders to when it comes to marketing, growth or go-to-market.In this episode, Elaine and On Deck co-founder Julian Weisser discuss how to decide what your startup should build first, what to consider when evaluating potential co-founders, how to think about fundraising in 2023, and the current capabilities of generative AI.Are you exploring starting a company? We’ve got a program for that.ODF has helped 1k companies get started and go on to raise over $2B. Applications for our 19th cohort in San Francisco are due this week. Learn more and apply at beondeck.com

On this episode of The Deep End, Julian Weisser – co-founder of On Deck – sits down with Marshall to discuss the latest from a program that has helped launch over 1,000 startups.Applications for the next cohort of On Deck Founders close on Tuesday, October 24th at 23:59 PST. If you’re exploring starting a company and want to figure out what to build and with whom, we’d love to chat.Apply today → beondeck.com 

Joining us in The Deep End today is Amrit Singh. Amrit Singh is the co-founder of Loop Health, the fastest-growing health insurance startup in India. Loop Health has raised over $40M, led by General Catalyst and Elevation Capital. As we delve deeper into the meta-series of longevity, we engage in a captivating conversation with Amrit, exploring how Loop Health incentivizes health for its users. We'll also venture into the exciting frontiers of the longevity movement and the pivotal role health insurance plays in ensuring our well-being for the long term.

Joining us today in The Deep End is Wallace Torres. Wallace is the Co-Founder of WellTheory. WellTheory is an early-stage startup with a pretty powerful mission: combating the autoimmune epidemic through the use of food as medicine, community care, and personalized insights based on health data. During our conversation, we delve into the story behind WellTheory and the positive impact the startup has had on its customers: helping them decrease fatigue, minimize pain interference in their daily lives, and achieve higher overall life satisfaction. We also explore the various models present in the digital health space, take a closer look at WellTheory's recent pivot towards partnerships, explore the importance of community in the digital health space, and reflect on the challenges of implementing and sustaining community spaces effectively.

Joining us today in The Deep End is Viswa Colluru, the CEO & Founder of Enveda Biosciences. Enveda has raised $175M in their quest to translate nature into medicine. Before founding Enveda, Viswa obtained a PhD in cellular and molecular biology, and started his career as a product manager at Recursion Pharmaceuticals. As our first guest in this series focusing on longevity and health, we speak to Viswa on why nature holds the great untapped potential for new drug discovery, why most drugs don’t work in human trials and what role artificial intelligence will play in unlocking biological and chemical data. We hope this conversation will give you a deep insight into nuances of the pharmaceutical industry, what the future holds for drug discovery and his advice for founders interested in this space.

Welcome to a new mini-series of The Deep End! In these mini-series we explore some of the most complex, societal problems facing us at the moment - helping listeners gain a nuanced understanding of a complex topic - and then be inspired and equipped to build, invest or support startups and founders that are aiming to solve these challenges. In the last mini-series, we looked at the meta-problem of access to housing. We looked at the main bottlenecks holding us back from achieving more accessible and affordable housing, and we spoke to the founders creating a new reality in this field. If you missed any of those episodes, head to wherever you find your podcasts and have a listen. For this mini-series, we are focusing on longevity: the pursuit of longer, healthier, and more fulfilling lives. The idea of living longer has captivated human imagination for centuries. While researching longevity, we identified eight bottlenecks holding us back from achieving longer and healthier lives, and we chatted with On Deck community members and founders to explore them.

Hey everyone, as we gear up for the launch of a new series on longevity next week, we wanted to re-publish this really timeley episode with Eugenia Kuyda, the founder and CEO of Replika, an AI companion company. Our conversation 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 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 become a part of our lives, not only in helping us do things but in supporting our emotional and social lives. Let's dive in.

Joining us today in the Deep End is Julian Weisser. Julian is the co-founder of On Deck, and a prolific angel investor with over a hundred angel investments including Loyal, Level, Atmos, and more. Every few months, we invite Julian to the podcast to get a sense of what's going on in the world of venture, and this conversation is not different. We look at the growing importance of profitability and revenue generation for investors, as well as the importance of founders aligning their trajectory with investor expectations. We also look at alternative funding models, with Julian discussing Zapier and Bubble’s model of prioritizing revenue and profitability over heavy venture funding. This episode is a must-listen for anyone interested in understanding the evolving venture capital landscape or thinking about fundraising.

Joining us today in the Deep End is Varun Bhanot. Varun is the co-founder and CEO of Magic AI, a home fitness system that uses AI to give you personalised training on a beautifully designed mirror. Prior to building Magic AI, Varun was the co-founder and CEO of Unhoused, a non-profit that leveraged technology to reduce homelessness. He also participated On Deck Founder’s third cohort. In this conversation, we discuss Varun’s approach to health & longevity. We cover his personal weight loss and gym journey, why European health tech startups have received less attention from the market and what the future holds for longevity companies.

Joining us in The Deep End today is Will Jarvis, co-founder and CEO of Valuebase. Valuebase is building land-centric models to improve property valuations and mass appraisal modeling. Valuebase recently secured $1.6 million in funding, with Sam Altman's Hydrazine leading the round and On Deck participating. Prior to Valuebase, Will served as a Researcher in Residence at On Deck, making today's conversation particularly noteworthy. As we continue our series on housing, we'll discuss the importance of land, Georgism and taxation, navigating the intricate world of ideas, and much more. Let's get started.

Joining us on The Deep End today is Ryan Delk. Ryan is the CEO & Co-Founder of Primer, a startup creating a new education system for children, centered around microschools. Last year, Primer announced that they’ve raised $15M in new capital. Ryan previously worked in Growth + Partnerships at Gumroad, and then joined another marketplace company, Omni, and became COO. In this conversation, we explore where the inspiration for Primer came from, how Primer is overcoming regulatory barriers in the space, and why Ryan believes the best education system is a world-class teacher in as small an environment as possible.

Joining us today in the Deep End is Lauren Self. Lauren is the founder of Roots Homes, a fractional home ownership company, that allows you to build equity in your home while paying rent, which recently raised a $2.2M seed round. In this conversation we explore how Roots is finding the missing middle between renting and buying, helping ensure home-ownership comes with flexibility and how Roots is increasing access to the American dream. ---- View the full series on Housing: https://www.beondeck.com/deep-end/housing

Joining us in The Deep End today for our housing series is Kim-Mai Cutler, a partner at Initialized who invests in proptech, real estate, and climate. Kim's background as a financial markets reporter and early-stage venture startup enthusiast, allowed her to broaden her reporting to include the intersection of the industry and public policy. In 2014, her essay on TechCrunch titled "How Burrowing Owls Lead To Vomiting Anarchists (Or SF’s Housing Crisis Explained)" sparked almost a decade of public advocacy that changed a number of state laws in California around housing and zoning. As our first guest for this housing series, it’s only fitting that we invited Kim to help us understand why housing is a key problem worth solving, what are the implications around the current state of things, and what different bottlenecks founders can work on. We hope this conversation will give you a nuanced understanding of a complex market and practical tactics for building in housing.

Over the past two years, we've interviewed 100+ people for our podcast, The Deep End. Now we're relaunching The Deep End as a multi-media publication, focused on problems worth solving. In the first series, we are tackling an issue that affects us all: access to housing. Our house provides us with a sense of belonging and serves as a sanctuary where we can retreat from the chaos of the world. Once we accept the importance of housing, our focus needs to shift to how we can make it more accessible. We kick off the series with an introduction to housing as a problem. We look into why it's a problem worth solving and what are the bottlenecks to doing so – technology, culture, regulation, and more. Then, over the next few weeks, we talk to Lauren Lorraine Self from Roots Homes, Kim-Mai Cutler from Initialized, Will Jarvis from ValueBase, Peter Light from Lumen Energy and Riley Meik to understand the bottlenecks to housing, and explore possible solutions. Through this, we try to form a mental map of the problem: understanding its societal importance, the current bottlenecks to progress and setting out some of the most impactful solutions. In doing so, we hope to give the audience the tools and knowledge to build, invest or support some of the solutions to these challenges. Housing is not an easy problem to solve, but we believe it is a problem worth solving. So let’s get going. Episodes notes and more: https://beondeck.com/deep-end/housing

Joining us in The Deep End today is Vignan Velivela. Vignan is the co-founder and CEO of AtoB, a fintech payments platform modernizing the trucking industry’s financial system, which raised a $155M Series B last year. He was also a part of the On Deck Founders’ third cohort. We are taking a short break from our series on access to housing, to talk to Vignan about one of the biggest challenges facing us at the moment: transportation and logistics. In this episode, we cover the central and essential role of trucking in America’s economy, why the trucking industry’s financial systems were ripe for disruption, how far away we are from self-driving trucks, and what the future of transportation looks like in the coming years.

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.

Navigating the Idea Maze to The Unlikely Birth of FinchFinch, a platform providing a unified API for employment data, was born out of failure and uncertainty. Ansel Parikh and Jeremy Zhang, the co-founders, first met during On Deck's second cohort. Both were passionate about solving the plumbing behind big problems and gravitated towards challenging infrastructure issues.Finch was born out of failure. Initially, they attempted to launch an embedded lending platform, but the COVID-19 pandemic disrupted their plans. Banks and customers began rejecting them as the future of lending became uncertain. Who was going to give a loan in such an uncertain environment? It wasn't until a small business lender they were potentially going to work with approached them with a request to help access employment data for the Payment Protection Program (PPP) that they discovered the opportunity that would eventually become Finch.Although the PPP was nearing its end when they built their solution, Ansel and Jeremy received enough positive feedback to continue pursuing the employment data problem. They embraced a "hard to get information made legible" business model, rather than following a thesis-driven approach. This allowed them to quickly pivot and adapt based on their unique founder-product fit: Ansel's background in fintech and infrastructure investments, combined with Jeremy's engineering and product experience, enabled them to quickly develop a product and secure their first customer. They emphasized the importance of failing quickly and focusing on the problem, rather than falling in love with a particular solution. Ansel also highlights that there is no “perfect moment” to get to conviction, you just need to make a decision.Finding the Right Co-FounderFor Ansel and Jeremy, finding the right co-founder was critical to their success. On paper, they had a unique founder / product fit.Jeremy had a background on engineering and product, and had worked on API challenges before that transferred to employment data ecosystems and the work they were doing at Finch.Ansel had been a late-stage investor at Kleiner Perkins and had spent a considerable amount of time on fintech and infrastructure investments so he was deeply familiar with the space.That said, they had to test whether they actually worked well as a team. They recommend setting up a three-week sprint with a potential co-founder to work on a project together, setting daily goals, and discussing progress. On top of that, they found another co-founder team who were going through the same stage and became accountability buddies. In their case, On Deck played a crucial role in helping them meet and build a strong working relationship because it provided with the structure they needed throughout that period.Embracing Complexity and Turning Illegible Information into Legible DataFinch's business model revolves around transforming illegible, hard-to-find information into legible, connected, and programmable data. The challenge of building a single source of truth for employer-employee relationships lies in the uniqueness, obscurity, and hyper-dynamic nature of these connections.Employment relationships vary significantly across industries and sectors, with different structures and incentives. Blue collar vs. White collar is not the only distinction. As an example, startup employees value equity, other type of non-tech companies value benefits, and factory workers value overtime.Moreover, employment data is often hidden in obscure systems that don’t communicate with each other, making it difficult to access. Adding to the complexity, this information is continuously changing, and outdated data is often used for critical decision-making at various levels.The US tax system and the US employment rules are a nightmare. There are different tax brackets and regulations at a city, state and federal level, and they also vary across industries. By focusing on making illegible information legible and valuable, the company offers a playbook for others looking to build successful businesses in the face of adversity.

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, 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 sets them apart from their competitors, and they should be intentional about raising venture capital. As the market returns to normal, Sasha advises founders to be aware of business compliance and financial diligence to avoid giving away a larger percentage of their company for less money. Throughout the episode, he emphasizes the importance of founders understanding their business numbers to make informed decisions and build successful companies. You can learn more about Puzzle at https://puzzle.io.

Joining us on 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.

On the latest episode of The Deep End podcast by On Deck, we interview our very own David Booth, CEO of On Deck.Recently, David has announced one of the biggest updates to On Deck since the program went virtual in 2020, with the return of in-person programming and community space in San Francisco.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.The episode is for anyone interested in better what is needed for early-stage start-ups to succeed in the current economic climate, the Bay Area as a tech hub, and how startups are the best mechanism we have to solve complex societal problems.

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. Learn more about Heyo here: https://heyo.at/

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 interesting – but hard – problem to solve, and how a platform like Odyssey has the potential to address fundamental inequality across the US school system. This episode is for anyone interested in new possibilities at the intersection of edtech and public policy.Learn more about Odyssey here: https://www.withodyssey.com/Keep up with Joseph Connor here: https://josephjconnor.com/

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.Learn more about Capital here, and watch the video Marshall and Andrew discuss here.Follow Andrew Rea on twitter.Learn more about New York Tech Week here.

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 asking for anything in return, alignment via equity, and decoupling where you live from where you work.

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 the value of those curation tokens goes up. With this protocol, reactions are brought on-chain instead of being tied to a platform like Twitter or Instagram. This creates a permanent, portable reputation system for NFTs that benefits both creators and the fans who’ve invested in them. We also talk about the growth of web3 and how NFTs are entering the zeitgeist, and the history of the term “curator”: what does it mean to be a curator, both in-person and digitally, and how has this definition changed over time? Going beyond digital art, we talk about how RARA social could integrate with music platforms, rewarding creators and curators alike for generating popular music and engaging playlists. This is a great episode for fans of NFTs and all things web3, as well as any creators out there, or curators who love finding and spreading great content out to their network.Follow Lawson Baker at @lwsnbaker and RaRa at @rara_social

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, identifying new problem areas in less-talked-about spaces like deathtech, or anyone, regardless of industry and age, who is interested in being a founder. Download and discover Chptr hereFollow Rehan’s founder journey on Twitter

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.Show links:On DeckFounder Fellowship: https://www.beondeck.com/Angel Fellowships: https://www.beondeck.com/angelsJulian Weisser’s links:Twitter: https://twitter.com/julianweisserPersonal Website: weisser.ioCompanies MentionedTraba - Reliable on-demand staffing. Co-founders met via On Deck. Podcast episode with CEO with Mike ShebatPrimer - Education for ambitious and curious kids. Co-founders met via On Deck. Podcast episode with CEO with Ryan Delk.People MentionedSander Daniels - Co-founder of Thumbtack and LP in Other VenturesRyan Delk - Founder of Primer

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 first product.Follow On Deck on Social Media for the latest on the future of work and education:https://twitter.com/beondeck/https://linkedin.com/company/beondeck/https://facebook.com/ondeckhq/https://instagram.com/beondeck/

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. - In the future, music labels will become much more competitive for artists than they have been in the past.

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 become a part of our lives, not only in helping us do things but in supporting our emotional and social lives.Hosted by Marshall Kosloff and produced by Jackson Steger

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 echo some of the observations that Nikhil Krishnan highlighted in our episode on overcoming the six stages of health tech grief that we released back in December.Hosted by Marshall Kosloff and produced by Jackson Steger

Amrit Singh is a co-founder of Loop Health, the fastest-growing health insurance startup in India. Our discussion today is about what it’s like to be a founder in India, and what the startup ecosystem there looks like relative to the US. India is an interesting paradox because although it’s a massive country in terms of population which contains almost 1 in 5 living people, that doesn’t always equate to huge market sizes in terms of available spend. We also talk about the state of healthcare in India in a world where medical inflation is leading to the cost of care doubling every five years even though quality isn’t getting 2X better, and how the fee-for-service model perpetuates perverse incentives in healthcare all around the world. We discussed Loop’s mission to help change this with a philosophy around value-based healthcare that focuses on preventing sickness instead of reacting to it. This episode is for anyone interested in company-building in emerging markets like India, or for those just looking for valuable insights on being a founder and what it takes to succeed. Let’s dive in.Hosted by Marshall Kosloff and produced by Jackson Steger

Joel Alexander is the founder and CEO of Crowdpad, a tokenized community-building platform for creators whose goal is to help creators monetize on day one. Our conversation today centers around web3 and the future of the creator economy. We discuss how the path to monetization on traditional creator economy platforms like YouTube is so long and onerous that most people give up, and how allowing creators to launch their own token to distribute out to their fans and building token-gated communities might help resolve this. We also discuss the disparity of earnings between the average web3 creator and the average creator on a platform like Meta, the best way of empowering independent artists with recognition and remuneration, how funding creators via social tokens vs. cash donations aligns incentives and makes the “hundred true fans” thesis viable, and how TikTok is one of the most discovery-friendly mechanisms in the world right now for all kinds of creatorsWhether you’re a founder or investor interested in the next iteration of the creator economy, or you’re just an aspiring individual creator looking to understand the landscape and the best tools available to reach and monetize an audience in 2022, this is the episode for you.Hosted by Marshall Kosloff and produced by Jackson Steger