Host Michael Sonnenfeldt concludes Season 1 with a retail legend and world-changing philanthropist, TIGER 21 Member David Jaffe. David’s mother Roslyn founded Dressbarn in 1962. David joined the family business in 1992. As CEO, David took the company from $1 billion in sales all the way to $7 billion as Ascena Retail Group, Inc., a Fortune 500 retailer with eight distinct brands including Ann Taylor, Loft, Lane Bryant, Catherines, and Justice, with over 4,500 stores across the U.S. and Canada, employing 65,000 associates.

In 2019, David transitioned out of Ascena. Today, he's a philanthropist on a quest for social change, leading two different nonprofits. David shares insights on family business succession, integrating philanthropy, and his advice for those transitioning out of their primary careers. Key topics include the evolution of Dressbarn, strategies for successful acquisitions, and the importance of aligning career choices with personal passions.

Video clips:

The 10-Year Rule for Family Business

"After My Exit, I Became the Wrong Kind of Investor"

Topics:

(00:00) Podcast announcement (Season 1 finale)

(00:31) Introduction to David Jaffe  

(01:00) Early career 

(02:27) Philanthropy and social change  

(03:13) Family business dynamics  

(04:28) Career transition  

(19:58) Lessons from leadership and mentorship  

(23:12) End of an era at Ascena

(25:50) The day after retirement  

(27:46) Exploring new opportunities  

(28:40) Advanced Leadership Initiative at Harvard  

(29:13) Combining passions: education and environment  

(30:21) Advice for post-career transitions  

(31:09) Investment lessons learned by Michael Sonnenfeldt and David Jaffe 

(34:04) Philanthropic ventures: FARE and Subject to Climate

(35:50) Balancing nonprofit and personal life  

(38:30) Partnerships

(40:40) Impact and future goals  

(46:27) Personal reflections and advice  

(49:37) Tip Jar

About:

TIGER 21 is the premier peer membership organization for ultra successful entrepreneurs, investors, and executives.

Tip Jar:

Dad’s Ten Rules

Salman Khan: "Brave New Words"

Merrily We Roll Along

Stereophonic

Links:

tiger21.com

Michael Sonnenfeldt - LinkedIn | @mwsonnenfeldt

FARE foodallergy.org

Subject to Climate subjecttoclimate.org

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For blockchain to truly disrupt and advance the economy, Perianne knew that another kind of network is needed, one to connect industry and government to promote innovation, jobs and investment. TIGER 21 Member Perianne Boring is the Founder and CEO of the Digital Chamber, the trade association she founded in 2014, dedicated to representing and advancing blockchain technology. 

For her education and advocacy work in the field, which attracted more than 200 members to the Digital Chamber, including Accenture, Cisco, Microsoft, IBM, Fidelity, and Wells Fargo, Forbes named Perianne one of the America's Top 50 Women in Tech. And she was also named one of the 10 most influential people in blockchain by Coindesk.

Host Michael Sonnenfeldt speaks with Perianne, a pioneering figure in the blockchain realm. “Bitcoin is the best performing asset class in the history of the world,” she explains. The investment community is just starting to understand the value of digital scarcity. They discuss her early entrance into the Bitcoin ecosystem, the economic disparities motivating her career, and the significant impact of her policy work.

The episode covers timely topics such as the technology behind Bitcoin, its geopolitical significance, and common misconceptions about its use. Additionally, Perianne shares insights into her personal journey and what sets her apart as an entrepreneur.

Video clips:

"Washington bet against me"

Most Influential Woman in Blockchain

Topics:

(00:00) Introduction to Perianne Boring

(05:10) How Perianne became influential in blockchain  

(06:49) Bitcoin's breakout year: 2013  

(09:11) Background

(11:08) GFC 2008  

(12:52) White House internship

(13:44) Bitcoin: Tech innovation  

(17:02) Myth-busting: Bitcoin and illicit finance 

(23:00) Personal reflections 

(24:19) FTX insights, need for regulatory frameworks  

(29:30) Mission and Bitcoin for financial sovereignty  

(32:13) Marshmallow test, delay gratification

(34:14) Mentorship, family  

(36:28) Not money-motivated

(40:00) Future of Bitcoin

(41:28) Perianne's future goals

(44:18) Leisure, health  

(43:22) Tip jar

About:

TIGER 21 is the premier peer membership organization for ultra successful entrepreneurs, investors, and executives.

Email questions or comments: [email protected]

Links:

tiger21.com

@mwsonnenfeldt

@PerianneDC

DC Blockchain Summit '24 | Life, Liberty, and Digital Property with Perianne Boring

https://digitalchamber.org/

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“You can’t un-feel it and you can’t un-remember it.” TIGER 21 Member Dylan Taylor is Chairman and CEO of Voyager Space, a multi-national space exploration company focused on building the next generation of space infrastructure. Dylan is not only a visionary leader in the New Space sector but also a commercial astronaut and philanthropist. Recognized globally for his pivotal role in the private space industry, he is the founder of Space for Humanity.

Dylan Taylor describes space flight and much more in this moving conversation with host Michael Sonnenfeldt. Surprisingly, for decades Dylan's career had nothing to do with space. Hear the question that identified his purpose.

From experiencing childhood hunger to his remarkable corporate rise, Dylan’s journey is nothing short of extraordinary. As a Fortune 1000 executive for multinational companies including Honeywell and Colliers, he had P&L responsibility in excess of $2B with 15,000+ employees in 60+ countries. We explore Dylan’s shift from a traditional career to founding Voyager Space Holdings and his transformative suborbital flight with Blue Origin. This episode covers how to find the work you're meant for, space exploration, as well as wealth creation, the purpose of business, and what makes a meaningful existence on our blue pebble.

Watch clips:

"Successful" but Miserable

Profound Emotions of Space Flight

"Why pollute Earth to go to space?"

Topics:

(0:00) Introducing Dylan Taylor  

(7:39) MBA, early career  

(11:47) Real estate, leadership roles  

(17:24) Discovering passion for space  

(23:52) Founding Voyager Space

(28:22) Experiencing spaceflight  

(32:44) Expanding access to space  

(36:10) Mentorship, goals  

(37:12) Dealing with different perspectives  

(42:30) TIGER 21 community

(44:02) Life lessons, family

(46:09) Milton Friedman vs new age business

(48:24) Tip Jar

About:

TIGER 21 is the premier peer membership organization for ultra successful entrepreneurs, investors, and executives.

Email your comments: [email protected]

Tip Jar:

“Man’s Search for Meaning” - Viktor Frankl

The Last Lecture

Links:

tiger21.com

x.com/mwsonnenfeldt

voyagerspace.com

x.com/dylan

dylantaylor.org

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Join host Michael Sonnenfeldt exploring the remarkable journey of Libby Connolly Alexander. In 1984, Tulane graduate Libby joined her father's startup. This small family venture evolved into a global giant and leader in recovery auditing for healthcare, retail, and more major industries.

How it began: Libby's father James Connolly, a former senior executive at Gimbels, recognized an untapped opportunity to help department stores recover overcharges. He started Connolly from his living room in 1979. Over the years, alongside her brother Larry Connolly and husband Robert Alexander, Libby took the reins as CEO, transforming Connolly, Inc. from $5 million to $5 billion during her tenure. It became a leader in recovery auditing. For example, Connolly, Inc. saved clients $1.1 billion in 2018-2019 alone.

Key Themes:

-Sustaining 20% annual growth for over 20 years (Warren Buffett-like returns)

-Family business: Second-generation success

-Insights on entrepreneurial risk, growth, and legacy

Libby's story underscores the power of humility and teamwork, offering valuable lessons for entrepreneurs. Tune in to hear how she built an industry-dominating company and the unique skills required to sustain such extraordinary success.

Watch clips:

How Connolly Achieved Warren Buffett-Like Returns With No Debt

A Real Life MBA from My Father

Valued $11 billion: Why we sold Connolly (Cotiviti)

Topics:

(0:00) Introduction: Connolly and recovery auditing

(6:38) Libby's father's career transition  

(10:45) Evolution of retail from Gimbels era

(15:08) Building a sustainable business model (value proposition)

(21:00) Libby joins Connolly (1984)

(22:30) Low noise

(25:00) Giving up a million dollars

(27:21) Libby and Larry take the reins

(29:57) Second generation family business

(31:57) Culture  

(34:22) PC revolution and competitive edge

(39:21) Healthcare  

(46:15) Selling to Advent  

(50:41) Reflections and legacy

About:

TIGER 21 is the premier peer membership organization for ultra successful entrepreneurs, investors, and executives.

Tip Jar:

Practice self care.

Links:

tiger21.com

Michael Sonnenfeldt - LinkedIn | @mwsonnenfeldt

libbyconnollyalexander.com

linkedin.com/in/libbyconnollyalexander

Book: “Figuring It Out”

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Martin Hermann is a serial entrepreneur with over 27 years of experience in the solar, clean-tech and high-tech industries. He has closed business transactions in excess of $5.3 billion. By the age of 35, Martin sold the software company he co-founded to Intel. Martin founded 8minutenergy, one of the largest independent developers of solar PV in the U.S. Join host Michael Sonnenfeldt to meet this TIGER 21 Member who is a global leader in renewable energy.

Martin is the CEO of BrightNight, one of the most promising companies helping to drive the energy transition to clean power. Its pipeline today consists of over 30 gigawatts of clean power projects. For context, that would power over 20 million buildings and represent over 10% of total renewable power in the U.S. today.

Martin has spent his career identifying fast-growing market opportunities to create significant value. He shares insights into renewable energy, including the development of hybrid power systems combining solar, wind, and battery storage to provide round-the-clock energy.

Watch clips:

From apprentice to founder: I sold to Intel

How I became a leading solar developer

How One Startup Surpassed 37 Other Intel Acquisitions

Closed 8minutenergy Thursday, Started BrightNight Friday

Topics:  

(0:04) Introduction

(4:16) How Michael Sonnenfeldt and Martin met

(5:45) Leading solar developer, 8minutenergy

(10:17) Formative years in Germany

(12:00) Entrepreneurial drive

(13:00) Software startup sold to Intel

(17:40) Partnership

(23:40) 2009: next venture, solar modules

(28:29) Lessons learned at Intel

(33:00) 8minutenergy to BrightNight

(41:00) BrightNight operating scale: 30 gigawatts of clean power projects

(45:08) Mindset: peak of career? What’s next?

(48:00) Tip jar

About:

TIGER 21 is the premier peer membership organization for ultra successful entrepreneurs, investors, and executives.

Tip Jar:

Why We Sleep - Matthew Walker

Links:

tiger21.com

Michael Sonnenfeldt - LinkedIn | X: @mwsonnenfeldt

Martin Hermann - LinkedIn

BrightNight

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Howard Morgan’s inimitable career began with his early and prescient interest in computers. In fact, Howard has been on email for 51 years! He is currently the Chair and General Partner of B Capital. He is considered one of the pioneers of early-stage investing, having co-founded First Round Capital alongside Josh Kopelman, which was the first professional seed stage fund and the first institutional investor in Uber.

Prior to First Round, Howard helped found Idealab with Bill Gross, and served as President of Renaissance Technologies, which he co-founded with Jim Simons. Renaissance Technologies is the best performing investment firm of all time, and its mysterious and famous Medallion Fund is considered to be the most successful fund ever.

Howard shares insights into the importance of timing, choosing great partners, and his approach to investments, mentorship, health, and philanthropy. Listen in on host Michael Sonnenfeldt’s conversation with the globally recognized venture capitalist, visionary, and TIGER 21 Member Howard Morgan.

Watch clips:

Behind Howard Morgan's Success

How to accomplish almost anything

Birth of RenTec

Topics:

(0:41) Host Michael Sonnenfeldt introduces Howard Morgan

(4:29) Howard Morgan's Journey: From Academia to RenTec

(7:15) Renaissance Technologies: Pioneering Quantitative Investing

(12:53) VC Successes: First Round Capital to Uber

(14:10) “You can accomplish anything if you don’t care who gets the credit.”

(16:01) Philosophy of Success: Mentors, Investments

(22:30) Aging, Dr. Comite

(24:25) Heliogen

(27:50) Ideally, Blastoff, and Timing Matters

(31:18) How Howard Morgan Evaluates an Investment

(32:11) First Round Capital, B Capital Approach

(34:54) Health: Biological Age 11 Years Younger

(37:45) Philanthropy: Generational Wealth, Impact, Legacy

(42:13) Tip Jar

About:

TIGER 21 is the premier peer membership organization for ultra successful entrepreneurs, investors, and executives.

Links:

tiger21.com

Michael Sonnenfeldt - LinkedIn | @mwsonnenfeldt

@HLMorgan

Related: Renaissance Technologies - Acquired

“Why The F We're Still Doing This”

The Discoverers - Boorstin

The Anxious Generation - Haidt

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On this podcast we explore paths to extraordinary success and what's next for those who have reached the pinnacle of accomplishment and continue to make a lasting impact in the world around them. This Season, join host Michael Sonnenfeldt, Founder and Chairman of TIGER 21, the premier peer membership organization for ultra-successful entrepreneurs, investors, and executives. Listen in on Michael's conversations with a curated group of TIGER 21 Members.

Featured guests in Season 1 include legendary venture capitalist and investor Howard Morgan, leading renewable energy entrepreneur Martin Hermann, author and distinguished payments integrity executive Elizabeth "Libby" Connolly Alexander, Voyager Space CEO and Chairman Dylan Taylor, and more.

If you have met one TIGER 21 Member, you have met one TIGER 21 Member.

Enjoy NEXT with TIGER 21 wherever you get your podcasts. Watch clips on our YouTube playlist. Learn more at tiger21.com/podcast.

Hosted on Acast. See acast.com/privacy for more information.