Founder's Dilemmas
The podcast is based on a best-selling book, The Founder’s Dilemmas, and is grounded in rigorous research into how to avoid the typical startup pitfalls. Co-hosted by Dean Dr. Noam Wasserman (Yeshiva University's Sy Syms School of Business) and Charlie Harary (entrepreneur, CEO, professor and radio host).
Episodes
45 episodes
Inside the Top Startup Accelerator, Y Combinator: YU founders Ken Book & Ari Wax of Fluid (Part 2)
Ken Book and Ari Wax go deeper inside the “black box” of the Y Combinator process, explore how the process changed them as founders regarding assessing the quality of their ideas and the speed with which they operate, and describe the way in wh...
•
Season 3
•
Episode 13
•
27:58
Inside the Top Startup Accelerator, Y Combinator: YU founders Ken Book & Ari Wax of Fluid (Part 1)
YU students Ken Book and Ari Wax gave up top investment banking opportunities to pursue their startup idea, persevered through rejection from investors and accelerators, and then achieved their dream of being accepted to the top accelerator in ...
•
Season 3
•
Episode 12
•
24:26
An IDF Veteran Founds a Drone Startup…then Again Founds 15 Years Later: Asaf Gilboa’s Insights #2
IDF veteran, Harvard MBA, and now serial entrepreneur Asaf Gilboa continues taking us through the most important lessons he has learned. They include: “We need strong views lightly held,” “’You can do anything but not everything’ is very ...
•
Season 3
•
Episode 11
•
28:31
An IDF Veteran Founds a Drone Startup…then Founds Again 15 Years Later: Asaf Gilboa’s Insights #1
IDF veteran and Harvard MBA Asaf Gilboa takes us through the most important lessons he learned as a young founder, then honed while working for Amazon and Bridgewater Associates (with their very different mindsets and cultures), and is now appl...
•
Season 3
•
Episode 10
•
24:39
Multi-exit founder Eli Portnoy, Pt. 2: How to Make Your Startup Fundable, How and When to Sell
Eli Portnoy, who has founded and sold two significant startups and is working on a third, continues with how to develop an initial idea into a company that will be of interest to venture capitalists, takes us inside the process and challenges o...
•
Season 3
•
Episode 9
•
33:52
Multi-exit founder Eli Portnoy, Pt. 1: Why Founders Need an MBA, How to Find & Hone a Big Idea
Eli Portnoy, who had TechStars’ biggest exit at the time and recently sold another important company, delves into why as an experienced entrepreneur he still went back to school to get an MBA, and the process he has developed to find three very...
•
Season 3
•
Episode 8
•
26:17
Inside Israel’s Largest Startup Incubator, with MassChallenge-Israel Director Yonit Serkin, Part 2
In these two episodes, former managing director Yonit Serkin takes us inside her career path to becoming the head of Startup Nation’s largest incubator, the application process for being admitted to MassChallenge, what separates the ones that m...
•
Season 3
•
Episode 7
•
26:42
Inside Israel’s Largest Startup Incubator, with MassChallenge-Israel Director Yonit Serkin, Part 1
In these two episodes, former managing director Yonit Serkin takes us inside her career path to becoming the head of Startup Nation’s largest incubator, the application process for being admitted to MassChallenge, what separates the ones that m...
•
Season 3
•
Episode 6
•
28:54
Inside Angel Investing, Pt. 3: Building a Portfolio, Managing Your Investors, 2023 Business Climate
A three-part series breaking down the lunchtime panel from Dean Wasserman’s Angel Investor Bootcamp, which was moderated by Charlie Harary and featured angel investor Moshe Neuman (Valued Ventures), entrepreneur turned investor Andrew Ack...
•
Season 3
•
Episode 5
•
31:04
Inside Angel Investing, Pt. 2: Decision-making Challenges & Solutions, Due Diligence on Founders
A three-part series breaking down the lunchtime panel from Dean Wasserman’s Angel Investor Bootcamp, which was moderated by Charlie Harary and featured angel investor Moshe Neuman (Valued Ventures), entrepreneur turned investor Andrew Ack...
•
Season 3
•
Episode 4
•
32:36
Inside Angel Investing, Pt. 1: Evaluating Founders, Mistakes and Regrets, Difficult Conversations
A three-part series breaking down the lunchtime panel from Dean Wasserman’s Angel Investor Bootcamp, which was moderated by Charlie Harary and featured angel investor Moshe Neuman (Valued Ventures), entrepreneur turned investor Andrew Ackerman,...
•
Season 3
•
Episode 3
•
40:08
Waze Cofounder Uri Levine, Part 2: S3E2: Waze Cofounder Uri Levine, Part 2: $1B Sale to Google, Founder Motivation, Fundraising Caution
In Part 2 of his interview with Charlie Harary and Dean Noam Wasserman, Waze cofounder Uri Levine describes why the team initial refused Google’s offer then accepted a revised one six months later, the founding motivations of frustration and re...
•
Season 3
•
Episode 2
•
32:39
Waze Cofounder Uri Levine, Part 1: Seizing an Idea, Assessing It, and Building a Founding Team
In this interview with Charlie Harary and Dean Noam Wasserman, Waze cofounder Uri Levine delves into the inception of the idea, the difficulty but importance of focusing on solving a problem rather than pushing a solution, and founding-team dyn...
•
Season 3
•
Episode 1
•
29:00
The Challenges of Founding a Non-Profit, Part 2: Dr. Jonathan Donath of Daily Giving
Dr. Jonathan Donath delves into leadership and entrepreneurial lessons he learned from his two founding experiences. He discusses the evolution of his professional career as a chiropractor, his dilemmas about selling his practice, and his...
•
Season 2
•
Episode 16
•
26:27
The Challenges of Founding a Non-Profit, Part 1: Dr. Jonathan Donath of Daily Giving
After founding a successful private practice, Dr. Jonathan Donath had an idea for a non-profit that would collect $1 per day from thousands of donors and distribute the funds to a different recipient every day. That idea became Daily Givi...
•
Season 2
•
Episode 15
•
25:21
Listener Q&A – “Which founder’s dilemmas are applicable to low-tech businesses and startups?”
Charlie Harary and Dean Noam Wasserman explore which founder’s dilemmas are universal and which only apply to high-potential startups, with implications for for-profits vs. non-profits, small businesses, and family businesses. Prod...
•
Season 2
•
Episode 14
•
20:25
Listener Q&A - “Pivoting is a New Term for Failure”: Lessons from Instagram and Lean Startup
Charlie Harary and Dean Noam Wasserman tackle a listener question about the impact of pivots on the startup and the team, and examples of Lean Startup being applied at Sy Syms. Produced by Uri Westrich
•
Season 2
•
Episode 13
•
23:55
Can You be Innovative in a Regulated Industry, and Found a Tech Company Without Tech Expertise? Founder-CEO Gilles Gade of Cross River Bank
Prominent founder-CEO Gilles (Yaakov) Gade joins Charlie Harary and Dean Noam Wasserman (and the Sy Syms Honors Program students) again to discuss why an innovative visionary is attracted to regulated industries, how he was able to found tech-h...
•
Season 2
•
Episode 12
•
32:20
Can You Have Explosive Growth but Maintain Your Early Culture? Founder-CEO Gilles Gade of Cross River Bank
Prominent founder-CEO Gilles (Yaakov) Gade joins Charlie Harary and Dean Noam Wasserman (and the Sy Syms Honors Program students) to explore the power of focusing on values, how to maintain that focus despite explosive growth, how R’ Jonathan S...
•
Season 2
•
Episode 11
•
32:45
The Making of a Star CFO, Part 2: Julie Feder’s Path from Sy Syms to a NASDAQ IPO
Charlie Harary and Dean Noam Wasserman delve further into the aftermath of the IPO through which Julie Feder led Aura Biosciences, the challenges of career dedication and Julie’s solutions to those challenges, and finding meaning and impact thr...
•
Season 2
•
Episode 10
•
31:37
The Making of a Star CFO, Part 1: Julie Feder’s Path from Sy Syms to a NASDAQ IPO
Over the last three decades since graduating from Yeshiva University, Julie Feder has transformed herself from an accountant into the CFO of prominent non-profit Clinton Health Access Initiative (CHAI), then led Aura Biosciences to an Initial P...
•
Season 2
•
Episode 9
•
29:38
Q&A episode: “Could outsiders have been able to tell that founder-led FTX was going to get into trouble?”
Sparked by a question from an editor for Harvard Business Review, Charlie Harary and Dean Noam Wasserman analyze FTX’s founder, Sam Bankman-Fried, through the lens of Founder’s Dilemmas to uncover several red flags that should have wor...
•
Season 2
•
Episode 8
•
26:51
Q&A episode: “Is Elon Musk’s leadership of Twitter unprecedented?”
Sparked by a question from a reporter, Charlie Harary and Dean Noam Wasserman delve into founders who take over larger companies, the heightened challenges faced by Elon Musk, and the bigger-picture entrepreneurial dynamics at play.Emai...
•
Season 2
•
Episode 7
•
18:45
Entrypreneurship Part 2: Franchising as the Solution to “But I don’t have an idea”!
Brian Scudamore delves further into the upside and challenges of franchising as an option for becoming an entrepreneur, and adds great insights about balancing family life with business demands. Charlie Harary and Dean Noam Wasserman disc...
•
Season 2
•
Episode 6
•
21:24
Entrypreneurship Part 1: Franchising as the Solution to “But I don’t have an idea”!
Brian Scudamore, award-winning founder of 1-800-GOT-JUNK, delves into franchising as an option for becoming an entrepreneur, especially if you have strong execution skills but lack an idea. Charlie Harary and Dean Noam Wasserman probe Bri...
•
Season 2
•
Episode 5
•
33:42