The Hard Pivot

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.

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.

Samantha Rose is a 4x founder and the CEO of Endless Commerce, a platform helping brands scale in e-commerce. Before that, she founded Mvnifest and GIR: Get It Right, which was acquired by Pattern Brands in 2021. She’s also the Managing Partner at Hologram Capital.
In this episode, Samantha shares the hard lessons from building and scaling—why “if you build it, they won’t come” is brutally true, the challenges of turning an idea into reality, and what she learned about manufacturing the hard way.
This one’s packed with insights for anyone building from scratch!

Yaakov Zar is the founder & CEO of Lev, a workflow and data platform for commercial real estate that’s raised over $200M since it’s funding just 3 years ago. Before that he co-founded home services company Dispatch, which was acquired by private equity firm Vista Equity in 2018.
In this episode, Yaakov walks us through the ups and downs - and then downs and ups - of the Lev story. From raising a $70M Series C to laying off half the team just a few months later, he shares in detail the decisions and factors that shaped Lev’s trajectory.
This is one you won’t want to miss!

Eli Portnoy is the CEO of BackEngine and a serial entrepreneur who previously founded and successfully exited two companies, including Sense360 (acquired by Medallia) and Thinknear (acquired by Telenav).
Tune in as Eli tells us the exact moment - at a hackathon with his team - when he realized he wasn’t the right CEO for what they were building at Sense360, and how that triggered the realization on what they should actually build…which led to their acquisition by a public company.

Oren Charnoff is the Co-founder & CEO of Fondue, an eCommerce startup recently acquired by marketing juggernaut Postscript.
But just 9 months before they were acquired, Shopify called with the news that every founder dreads: they were launching a competing product.
Join us as Oren guides us through that fateful day, and how Fondue leadership rallied the team around an entirely new vision, building a business with millions of revenue in just a few months time.

Gilad Uziely is the co-founder & CEO of Sequence, a fintech startup backed with $7.5M from Aleph & Emerge Ventures that’s changing the way small businesses manage & utilize their cash flow. But before Sequence, there was Lance, a neobank Gilad & co-launched that got to tens of thousands of business customers before calling it quits. So what happened?Join us for this first episode of The Hard Pivot podcast as Gilad tells the story of how Sequence - like a phoenix - grew out of the ashes of the once-heralded Lance.

The Hard Pivot is a podcast where founders share their pivot stories—the tough decisions, challenges, and turning points that reshaped their companies.Inspired by the responses Zach 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.