The Deep End

On Deck

The Deep End by On Deck is a podcast where visionary builders, creators, and experts discuss world-changing ideas. We skip the surface level and go in depth into ideas that matter including the futures of commerce, higher education, art, governance, longevity, and more with some of the most exciting figures in these fields. The Deep End is hosted by Marshall Kosloff and produced by On Deck—where top talent go to accelerate their ideas and careers. Visit ideas.beondeck.com for show notes and additional essays.

  • 53 minutes 38 seconds
    Deep Dive: Find the right co-founder and idea with Mo El Mahallawy, CTO and co-founder of Shepherd

    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.com

    12 February 2024, 11:51 pm
  • 55 minutes 16 seconds
    Deep Dive: Shutting down a startup, doing right by your team, and founder identity with Stevie Cline (VC at Vol. 1 Ventures)

    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.com

    6 February 2024, 10:34 pm
  • 50 minutes 2 seconds
    Control Your Financial Destiny: Runway, Metrics, and more with Puzzle's CEO Sasha Orloff

    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.com

    For 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.

    19 January 2024, 5:39 pm
  • 1 hour 4 minutes
    Augmenting people with AI and building the future featuring Matt Rastovac of Respell

    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.com

    For 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.

    7 December 2023, 4:50 pm
  • 1 hour 8 minutes
    "The most important milestone in the history of longevity biotech" — Archival Interview with Celine Halioua (Founder/CEO of Loyal)

    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.com

    2 December 2023, 1:47 pm
  • 55 minutes 3 seconds
    Defense Tech: Opportunities to support America and our allies with veteran Mike Slagh (founder/CEO of Shift)

    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.com

    Without further ado, here’s my conversation with Mike Slagh

    11 November 2023, 9:41 pm
  • 21 minutes 46 seconds
    Lessons from the Journey to Building a Product Customers Want with Max Greenwald of Warmly

    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.

    27 October 2023, 6:19 pm
  • 39 minutes 28 seconds
    Generative AI and deciding what to build first with Elaine Zelby of Tofu

    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

    24 October 2023, 10:08 pm
  • 22 minutes 9 seconds
    Explore Starting a Company in San Francisco

    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

     

    23 October 2023, 7:45 pm
  • 30 minutes 11 seconds
    Raising $40M to Build Health Insurance for India with Amrit Singh
    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.
    16 August 2023, 4:00 am
  • 45 minutes 57 seconds
    Combating the Autoimmune Epidemic with Wallace Torres
    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.
    3 August 2023, 4:00 am
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