The Hard Pivot

Zach Roseman
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The Hard Pivot is where founders tell the stories of their pivots - the tough decisions, the turning points and the outcomes that reshaped their companies. Inspired by the responses host Zach Roseman got after publicly sharing Draftboard’s pivot journey, this podcast dives into the critical moments of change: when founders realized something was wrong, how they communicated with investors and teams, and how they charted a new course forward. Each episode offers honest insights and lessons from those who’ve faced the uncertainty of a pivot and emerged with a new path.

  1. 08/18/2025

    AIA with Israel Shushan

    Israel Shushan was toiling away as a junior employee at an electronics trading firm 15 years ago when he saw an opportunity: reselling products on the recently launched Amazon Europe problem.  His journey to AIA saw him build a 7 figure D2C brand (twice), launch a successful Amazon store consulting business, and finally ended with him blowing that business up almost overnight when he realized a related but wholly different opportunity existed in the Amazon world that he called home.  This is the story of AIA Assets, Israel Shushan's phenomenally creative business whose core philosophy is that Amazon stores are similar to physical stores in a way most others have yet to realize: they are true digital assets (the non-crypto kind). Join us as we delve into the world of platforms and probations, minutiae and marketing...

    1h 11m

  2. 08/11/2025

    Sutro with Ravi Kurani

    If you thought Ravi Kurani, founder of pool monitoring startup Sutro, was destined to go into the world of water analysis - you'd be wrong. But you'd also be right? Ravi's father built a chain of pool supply stores on the west coast, but Ravi was dead set on a career in defense. A detour to India to work on water purification changed everything.  Come hear the story of Ravi's quest to build Sutro; how it was so promising that a big Canadian conglomerate acquired it pre-release; and how he's now building an entirely new business based around Sutro's technology - but as a customer this time, not its founder.

    1h 1m

  3. 08/04/2025

    Candid Part 2 (Candid) with Nick Greenfield

    Nick Greenfield got a call from a hedge fund investor that changed his life: Invisalign's patent was about to expire - did Nick want to build a better version? That's when the rollercoaster began - and as you'll hear, it continues to the this day (on a massive upswing now!) From $50M in revenue in 3 years and Goldman Sachs banging down the door to talk about IPO to a complete pivot (and I mean complete) and total recapitalization - I think Nick's journey is truly peerless.  Join us for this tour de force through the go-go days of D2C in the late 2010s - and how it ultimately ended (and then rebirthed Candid as something even stronger).

    53 min

  4. 07/28/2025

    Candid Part 1 (Lyft) with Nick Greenfield

    Nick Greenfield, the founder of dental health startup Candid, has a story with more ups and downs than I've ever heard before.  But first a bonus episode: turns out Nick was an early member of the Lyft team back when it was still called Zimride. Join us for this blast from the past bonus segment where Nick tells us the origins of the pink mustache, how Sidecar was just a tad too early and how Uber became a juggernaut.  Part 2 where Nick tells us the (crazy/insane/bonkers) story of Candid is up next.

    25 min

  5. 07/21/2025

    Alma with Harry Ritter

    It's hard to describe Harry Ritter: yes, he's the founder and CEO of mental health juggernaut Alma - but he's also a doctor, a lawyer, a reformed McKinsey consultant and an early employee at Oscar Health.  Whatever you've achieved in life: know that Harry's probably done it too. But he also did something else: lift Alma up out of the depths of certain death in March 2020 when COVID hit and destroyed their entire business. Join us to hear how he brought Alma back from the dead and led it to becoming an almost $1 billion company over the course of just 2 years.

    1 hr

  6. 07/13/2025

    Hungry with Eman Pahlavani

    Eman Pahlavani, Co-Founder of Hungry, has a story to tell - and it's worth hearing.  2x founder, 2x pivots and a spinout along the way - Eman tells us about the early days of Hungry as a food delivery platform leveraging at-home chefs, and how that first $1,000 corporate order changed their business overnight from consumer to B2B.  Growth took off and everything was smooth sailing - until COVID lockdowns changed everything. And yet somehow, despite months of no revenue, they exited 2020 with a business doing millions each month in revenue - and kept growing from there. This story is a doozy - you won't want to miss it.

    50 min

  7. 03/17/2025

    Meetup with David Siegel

    David Siegel is the former CEO of Meetup and Investopedia, where he led major transformations, scaled operations, and navigated multiple exits. With deep experience in strategy, M&A, and turnarounds, he's built and grown businesses across e-commerce, digital media, and SaaS. In this episode of The Hard Pivot, David shares what it really takes to lead through change—whether it’s pivoting a business model, executing a high-stakes turnaround, or making bold moves to stand out (including one that involved a very unconventional interview tactic). A must-listen for anyone thinking about what it really means to adapt and win.

    1h 5m

  8. 03/03/2025

    MaestroQA with Vasu Prathipati

    Vasu Prathipati is the co-founder & CEO of MaestroQA, a platform that’s redefining quality assurance in customer experience. Under his leadership, MaestroQA has raised $35 million and built a product that helps companies deliver better customer interactions at scale. In this episode of The Hard Pivot, Vasu shares what it takes to navigate tough decisions as a founder—from building a team that refuses to quit, to questioning the very purpose of a pivot, to why VCs should be funding entrepreneurs, not just founders. This one is a must-listen for anyone scaling a company in real-time.

    1h 27m
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About

The Hard Pivot is where founders tell the stories of their pivots - the tough decisions, the turning points and the outcomes that reshaped their companies. Inspired by the responses host Zach Roseman got after publicly sharing Draftboard’s pivot journey, this podcast dives into the critical moments of change: when founders realized something was wrong, how they communicated with investors and teams, and how they charted a new course forward. Each episode offers honest insights and lessons from those who’ve faced the uncertainty of a pivot and emerged with a new path.

Information

  • Creator
    Zach Roseman
  • Years Active
    2K
  • Episodes
    14
  • Rating
    Clean
  • Copyright
    © Copyright 2025 All rights reserved.
  • Show Website
    The Hard Pivot