Founder's Dilemmas

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 which their association with Y Combinator has changed things for their startup, Fluid Markets. For links to other content from Charlie and Dean Wasserman https://linktr.ee/foundersdilemmas   

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 the world.  Learn their insights into battling Imposter Syndrome, how Y Combinator seems to decide which founders to admit, and what founders experience within Y Combinator. For links to other content from Charlie and Dean Wasserman https://linktr.ee/foundersdilemmas  

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 true for startups,” and “Don't build for miracles.” For links to other content from Charlie and Dean Wasserman https://linktr.ee/foundersdilemmas 

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 applying in his second startup 15 years later.  For links to other content from Charlie and Dean Wasserman https://linktr.ee/foundersdilemmas 

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 of selling your company, and delves into why he's diving into a third venture now (and with what new 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 different Big Ideas and hone them into salable companies.

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 make it, and the differences and challenges of being a founder in Israel vs. in the U.S.Produced by Uri Westrich

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 make it, and the differences and challenges of being a founder in Israel vs. in the U.S.Produced by Uri Westrich

 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, and founder Kumesh Aroomoogan of Accern (who has raised funding from nearly 200 angels). Produced by Uri Westrich  

 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, and founder Kumesh Aroomoogan of Accern (who has raised funding from nearly 200 angels). Produced by Uri Westrich   

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, and founder Kumesh Aroomoogan of Accern (who has raised funding from nearly 200 angels). Produced by Uri Westrich  

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 revenge, and his experiences with venture capitalists. Produced by Uri Westrich 

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 dynamics. Produced by Uri Westrich 

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 recent transition from owner of a private practice to employee in a larger healthcare company.Produced by Uri Westrich

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 Giving, which in 4 years has distributed $7.5 million to dozens of charities.  Jonathan discusses the lessons learned from both founding experiences and some of the unique challenges he faced along the way. Produced by Uri Westrich 

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. Produced by Uri Westrich 

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 

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-heavy Cross River Bank without having a tech background, and other founding challenges he has faced. Produced by Uri Westrich

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 Sacks zt”l shaped the founding of his company, and other founding dilemmas he has faced at Cross River Bank. Produced by Uri Westrich 

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 through a career in finance.Produced by Uri Westrich

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 Public Offering (IPO). Charlie Harary and Dean Noam Wasserman delve into her career decisions, typical career mistakes, and the path to an IPO.Produced by Uri Westrich

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 worried employees, investors, and policy makers.Produced by Uri Westrich

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.Email us your questions/comments!Foundersdilemmaspodcast@gmail.comProduced by Uri Westrich

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 discuss Brian's advice and its relevance for listeners.Email us your questions/comments!Foundersdilemmaspodcast@gmail.com

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 Brian's early decisions, his approach to undoing mistakes, and who should think about franchising as a business opportunity.Email us your questions/comments!Foundersdilemmaspodcast@gmail.com

Itamar Frankenthal continues his “entrepreneurship by acquisition” reflections.  Guided by Charlie Harary and Dean Noam Wasserman, he delves into the lessons learned from investigating potential companies to buy, his negotiations with the company owners and banks, and what he would do differently next time.Itamar Frankenthal, CEO of Rose Batterieswww.RoseBatteries.com

Lacking an idea with which to found a company, but having operating skills and a favorable stage of life, Itamar Frankenthal pursued “entrepreneurship by acquisition”: trying to buy an existing small company.  With Charlie Harary and Dean Noam Wasserman, Itamar delves into his motivations, the process, and key lessons learned.Itamar Frankenthal, CEO of Rose Batterieswww.RoseBatteries.com

Every cofounder will feel better about the team if s/he has a “Chief” title (Chief Technology Officer, Chief Marketing Officer, Chief Operating Officer, etc.).  Are there any downsides to doing so?  Charlie Harary and Dean Noam Wasserman delve into this decision, its long-term implications, and how it is a microcosm of other founding dilemmas.

Far fewer people start companies than want to do so and they wait a lot longer to do so than they planned.  When they found, it's often in the industry in which they have been working, causing unexpected barriers.  Charlie Harary and Dean Noam Wasserman shine a spotlight on how we cause problems for achieving our dreams and on some solutions.

In our first 15 episodes, Charlie Harary and Dean Noam Wasserman covered the founding lifecycle from pre-founding through exit, including lots of critical dilemmas faced in between and potential solutions to many of those dilemmas.  This brief highlight reel includes snippets from many of the episodes, giving a small taste of Season One before we head into our second season.  Enjoy!Clips in the order they are played:Episode 7:  “Should I Double Down On My Bet?”The Truth About Entrepreneurial PersistenceEpisode 3: relationship SolutionsEpisode 15: “Should I Sell My Baby?”Selling, Going Public, or Remaining IndependentEpisode 9: Equity Splits Q&A:Is the Idea Worth Anything?Episode 8: Financing Dilemmas and Rich vs. King TradeoffsEpisode 14: The Greatest Jewish Serial Entrepreneurof the Last 50 Years: Rav Noach Weinberg zt”lof Aish HaTorahEpisode 5: Reward Dilemmas: Splitting the EquityEpisode 11: ”You're Firing Me as Parent of My Baby?”:The Paradox of Entrepreneurial SuccessEpisode 2: Relationship ProblemsEpisode 10: Q&A: “Do Successful Founders Mislead Us?” On the YouTube version, each segment is labeled with its accompanying episode:https://youtu.be/2ZfoQA8M8Uw

How can you decide whether to sell your company or take it public? What are the business and often-sensitive personal considerations?  Charlie Harary and Dean Noam Wasserman examine the data and delve into the inside stories of the founders of Nike and of Nantucket Nectars.

R' Weinberg failed repeatedly before succeeding in founding Aish HaTorah, and attributed his success to those failures. What lessons did he learn about cofounding, pivoting, and managing his own growth aspirations? Charlie Harary and Dean Noam Wasserman explore actionable lessons.

First-time founders look forward to becoming experienced serial entrepreneurs. Are there pitfalls to being a serial entrepreneur? Charlie Harary and Dean Noam Wasserman delve into the data and the inside stories of the founders of Twitter and billion-dollar company New Relic.

After a founder is replaced as CEO, should s/he stay as a lower-level executive, or would thatbe the worst scenario? Charlie Harary and Dean Noam Wasserman delve into “The Day Afterthe Firing” and how that critical transition can be make-or-break for the startup & the founder.

Why do successful founders get fired? What are the early signs that it might happen to you?The paradox of entrepreneurial success is that your success might result in losing control andbeing replaced. Charlie Harary and Dean Noam Wasserman delve into this difficult reality.

A listener asks if it is worthwhile to read books about or by successful founders. Charlie Harary and Dean Noam Wasserman discuss the importance of reading with a critical eye, extracting parts we can emulate while avoiding implicit pitfalls & unrealistic aspects of the success.

Diving deeper into Rewards and founders' equity splits, Charlie Harary and Dean Noam Wasserman tackle listener questions: Is the startup's idea valuable, or is the value really “99% perspiration”? Should all 50/50 equity splits be avoided? 

One of the most important decisions is how to finance the startup.  For instance, self-fund or raise outside money?  Dean Wasserman introduces a structured way to think about this and other “Rich vs. King” tradeoffs you will face, and delves into it with Charlie Harary.

Does entrepreneurial persistence separate success from failure, or is it actually doubling down and digging yourself a deeper hole? Charlie Harary and Dean Noam Wasserman tackle the truth about persistence – virtue or vice? – in startups and in life.

Charlie Harary and Dean Noam Wasserman tackle listeners' burning questions about pre-founding and building the founding team. For instance, should you wait for the perfect time to found? Solo found or have three cofounders? Give equity to employees?

Along with allocating Roles, you have to allocate Rewards – most notably, ownership stakes. What are the pitfalls and best practices for doing so? A 50-50 split seems fair and simple, but does it breed success? Charlie Harary and Dean Wasserman tackle this contentious topic.

How should you allocate titles and how should you make decisions as a team? Your early decisions could result in gridlock, heightened tensions, inefficiency, and fighting. Dean Noam Wasserman and Charlie Harary dive into Roles and Decision Making dilemmas.

The relationships you tap in forming your founding team can introduce significant Playing With Fire risks for the team. Having covered the most notable of those risks in our previous episode, Charlie Harary and Dean Noam Wasserman delve into the best ways to reduce those risks.  What Firewalls can you build to protect your most cherished relationships from the damage caused by Playing With Fire? What are the best ways to proactively tackle the elephants in the room that you loathe to discuss? 

As an entrepreneur, is it more beneficial to go solo or work with a team? How important is trust when founding a company? Instinct tells us to found with a close friend or family member. However, the data surprisingly show a different story, with important implications for founding teams. Dean Noam Wasserman and Charlie Harary explore these critical relationship dilemmas.

What early decisions tend to go awry for entrepreneurs and are a major cause of failure? What are essential steps to take even before founding a startup? Dean Noam Wasserman and Charlie Harary use their extensive research and experience to help entrepreneurs anticipate the pitfalls that tend to sink startups while providing actionable insights into preparing to become a founder.