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Ryan Caldbeck on Entrepreneurship and the Importance of Lifelong learning

The Altogether Show with Eric Satz

Release Date: 07/02/2021

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The Altogether Show with Eric Satz

This episode was originally aired on February 12, 2021. Life isn’t always black and white, and sometimes the gray is controversial. This week’s guest firmly believes in staying true to himself, living by his grandmother’s maxim: “What other people think of you is none of your business.” In this episode, you’ll hear that come to life. When asked to describe himself, he said gratitude, resilience, and enthusiasm. This is a man who now has his own unit of time: A “Scaramucci.” Anthony was a successful entrepreneur, financier, and political player well before stepping up to the...

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The Altogether Show with Eric Satz

Despite the 280-character limit, Brian Feroldi has found a way to utilize Twitter as a profound tool for sharing insight into financial health and taking a money mindset. Whether on social media, , or , Brian is dedicated to discussing personal finance and investing in plain language that everyone can understand.   Brian Feroldi is a financial educator and writer focused on demystifying the stock market and promoting financial wellness. In addition to being featured on The Motley Fool, Brian recently published in April 2022.    In this episode, Brian shares his conservative...

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The Altogether Show with Eric Satz

A pair of headphones tangling in the spokes of a bike is one of the more unique inciting moments of an entrepreneurial venture. While his entrepreneurial spirit would lead him to Hong Kong and scouting factories in Southern China, it was Sheel Mohnot’s experience working in India with that would greatly influence his career as an investor. Impacted by the individuals he met, Sheel discovered a passion for investing in resilient and tenacious people. Sheel Mohnot is a seed-stage fintech investor, co-founder and GP of , and founder and GP of Fintech. Inspired to “work on hard problems'' by...

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The Altogether Show with Eric Satz

An In-N-Out burger might be the key to lasting, meaningful professional relationships. Popping out of the office to grab a bite to eat was one of the ways Rachael Horwitz bonded with colleagues in her early years at Google, and the relationships formed during these years would lead to incredible career opportunities in her future. Rachael Horwitz is a communications expert, currently serving as the Chief Marketing Officer at . Previously, Rachael was an Operating Partner at , and she has served on and led communications teams at Google, Facebook, Twitter, and Coinbase during major growth...

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The Altogether Show with Eric Satz

Shane Mac is particularly proud of one of the several successful companies he co-founded in the last 10 years: . Co-founded with his former assistant without venture funding, Squared Away connects military spouses with quality remote employment opportunities.  In addition to Squared Away, Shane is the co-founder and President of , founder and General Partner of , and a passionate writer and musician. He also co-founded and served as CEO of Assist, which was acquired by after merging with Conversocial. In this episode, Shane provides insight into his impressive trajectory, beginning with...

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The Altogether Show with Eric Satz

Moving to the United States from Milan in 2001—mere months before September 11—Lorenzo Thione was quickly forced to reckon with life’s lack of guarantees. The only life worth living was an authentic one. Coming out was a must, and he never looked back. Lorenzo Thione is an entrepreneur, technologist, venture investor, and producer making an impact across several organizations: , , , and . He is a resolute LGBTQ community advocate and dedicated to amplifying underrepresented voices and stories. In this episode, Lorenzo discusses co-founding StartOut and managing Gaingels, and their...

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The Altogether Show with Eric Satz

When was the last time you read Time cover to cover? This episode’s guest would read and discuss the magazine issues with her father every week as a child. It was an activity she didn’t quite appreciate at the time, but those in-depth discussions provided a foundation for understanding the world beyond Harlem and sparked a lifetime of curiosity and an industry-spanning career. Lorine Pendleton—investor, advisor, and attorney—started her career in the halls of , earned her law degree, and continued her path in startups until discovering an unsettling fact: Less than 1% of venture...

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The Altogether Show with Eric Satz

There's a lot of noise in the investment space—raving pundits, extreme headlines, and financial advertisements—and investors are susceptible. Long-term success requires learning to tune it out. This week’s guest is William Spitz, the highly decorated former Treasurer and Vice Chancellor for Investments at Vanderbilt University and co-founder and principal of . In this episode, Bill reflects on being immersed in environments of influential and innovative financial thinkers during his MBA at the University of Chicago and in the intercollegiate, collaborative atmosphere of his early years...

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The Altogether Show with Eric Satz

Promising ideas never really leave you. A visit to a tea auction in India was the missing ingredient Barry Nalebuff needed to create with his former student, Seth Goldman, five years after connecting over disdain for excessively sweet beverages. This week’s guest is renowned Yale School of Management professor, serial entrepreneur, and prolific writer Barry Nalebuff. Following the immense success of Honest Tea, Barry co-founded and . His most recent book, , was released in March. In this episode, Barry discusses his logical—"Spockian”—approach to negotiation and the key questions to...

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The Altogether Show with Eric Satz

Imagine navigating the deterioration of the mortgage market in 2007 and facilitating the most high-profile transactions of the financial crisis. Then, imagine that it’s March 2020, and you’re leading the SEC as the COVID-19 pandemic upends the global economy.  This week’s guest has chartered these choppy waters and emerged aiming the lessons of the past at our regulatory future. Jay Clayton served as the 32nd Chairman of the U.S. Securities and Exchange Commission and boasts a decades-long career at Sullivan & Cromwell, where he currently is a Senior Policy Advisor and Of...

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More Episodes

What does it take to go from small-town kid to successful CEO? To this week’s guest, the answer is simple: never stop learning. A self-proclaimed underdog with a burning desire to make an impact, Ryan Caldbeck describes himself as gritty and a dreamer. In this episode, Ryan discusses growing up in a small town in Vermont, becoming an NCAA basketball champion, finding success in private equity, and eventually co-founding (and stepping down from) CircleUp—and the role each played in his passion for tech entrepreneurship. 


Ryan’s small-town upbringing shaped his entrepreneurial spirit. From the time he was young, he would dream about accomplishing something amazing. As his dreams became a reality, though, he found himself struggling both personally and professionally. Reflecting on his journey in admirable detail, Ryan advocates for tapping into your network for support and stresses the importance of mental health.


As someone who is extremely curious and loves to learn and grow, Ryan felt stuck in his career in private equity. That all changed in early 2011, while sitting on a panel where no one could answer the question “How do you raise money for a $5MM business?” At that moment, he knew he wanted to start a company that was going to make an impact—and thus, CircleUp was born. Suddenly, he found himself surrounded by people who loved to learn just as much as him, and it was as if his whole life finally made sense.


In this episode, we talk about Ryan’s intense passion for human connectivity through learning, his journey to CEO, and his ultimate decision to step down. So, what’s next for this life-long learner? Listen to the full episode to find out.