In this episode of "20 minutes VC," host Harry Stebbings interviews Jerry Colonna, the CEO Whisperer and founder of Reboot, a coaching company aiding top entrepreneurs and investors. Colonna, a former partner at JPMorgan and co-founder of Flatiron Partners with Fred Wilson, shares his journey from VC to coach, emphasizing the importance of self-inquiry and aligning one's inner self with their professional life. He discusses his approach to coaching, the value of emotional rapport in mentorship, and the need for venture capitalists to examine their behaviors and embrace vulnerability to improve their relationships with entrepreneurs. Colonna and Stebbings also explore the challenges of work-life balance and the significance of listening to one's inner voice for personal and professional fulfillment.
This is the 20 minutes VC with your host Harry Stebings. And you can add me on Snapchat at H. Stebbings with two B's.
The quote introduces the host and provides his Snapchat handle for listeners to connect with him.
So joining me for this very special episode is Jerry Kelowna. Now, Jerry is without a doubt one of the most interesting guests I've had on the show. Jerry, or sometimes known as the CEO Whisperer, is a founder at Reboot, the coaching company that helps some of the world's greatest entrepreneurs and investors with the internal ups and downs in their life and support the growth they need to improve their performance.
The quote introduces Jerry Colonna and highlights his significant role in the entrepreneurial community as well as his previous accomplishments.
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I'm in my early twenty s and I'm a technology reporter for a magazine called Information Week. Didn't expect to be a technology reporter, expected to be a poet and writer. That was life. And I'd spent a couple of years as a reporter, then eventually news editor, and then eventually editor of that magazine. And then I became director of editorial technology, which put me directly in the path of trying to figure out what our non print strategy was to be.
The quote details Jerry's unexpected path from aspiring poet and writer to technology reporter, which eventually led him to venture capital.
Starting in around 2000, I had begun to re-experience a deep and profound existential depression. The depression that came on in my mid to late thirty s was different than the depression that I had struggled with in my late teen years and early twenty s. I had been very open about the fact that I had been suicidal in my teenage years, having been hospitalized at one point for an attempt.
This quote reveals the personal struggles that Jerry faced, which played a significant role in his career shift from venture capital to coaching.
"In the spring of 2001, I said, I can't continue. I can't do this. And it was painful because Fred continues to be an incredible friend, love and admire deeply, but I couldn't be his partner. I couldn't do it."
This quote highlights the emotional difficulty Jerry faced in leaving his partnership with Fred, indicating the deep personal and professional conflict he experienced.
"I somewhat mistakenly took a position at J. P. Morgan, thinking that that's all that I needed to do, was just sort of change the venue."
Jerry reflects on his mistake of thinking that changing his work environment was the solution to his dissatisfaction, which turned out to be incorrect.
"The transition to becoming a coach began during that time when I was doing my own work and basically saying, okay, I'm going to just sit here and figure it out."
Jerry's journey to coaching started with introspection and a desire to understand himself better, indicating a turning point in his career.
"I asked one of the questions that I've now become famous for, which was, why did you choose a law when obviously you hate it? And he started to cry."
This moment of asking a poignant question and eliciting a strong emotional response from the young attorney was a significant realization for Jerry of his innate coaching ability.
"The process of uncovering and unpacking what's truly going on for us, what I refer to as a radical self inquiry, is never a one and done thing."
Jerry explains that radical self-inquiry is a continuous process, suggesting that personal growth and self-awareness require ongoing effort.
"It's like all of a sudden this little whisper in the back of your head comes up and says, you should be a coach. What the fuck? I don't want to be a coach. No, you should be a coach."
This quote captures the internal conflict and resistance Jerry experienced before accepting his calling as a coach, illustrating the struggle between conscious desires and unconscious motivations.
"Generally speaking, we all compartmentalize in order to get through the day."
Jerry acknowledges that compartmentalization is a common strategy used to handle life's challenges, highlighting its short-term usefulness.
"When we live a life where we're constantly segmenting off the inner reality of who we are, and living with a mask where the outer does not match the inner over a prolonged period of time, that leads to a notion of disassociation."
This quote emphasizes the dangers of long-term compartmentalization, suggesting that it can cause a disconnection from one's true self and potentially lead to mental health issues.
"What I often suggest is work-life integration, and the connecting point being you."
Jerry proposes that integrating personal values with professional life leads to a more authentic and satisfying existence.
"If you live your life as an empathetic, caring, feeling, vulnerable human being, and then you walk into a work environment where those equalities not accepted, you are going to suffer."
Jerry points out the conflict that arises when personal traits are not welcomed in the workplace, leading to emotional and psychological stress.
"Fuck the goddamn playbook. Who the hell are you?"
With this emphatic statement, Jerry urges individuals to prioritize authenticity over conforming to industry expectations, advocating for a personal approach to professional life.
"When we live our life according to what other people expect us to be, we die a little bit every day."
This quote emphasizes the detrimental impact of living a life that prioritizes others' expectations over personal authenticity.
"I think that many investors mimic the most aggressive behaviors as a way to cover their fundamental insecurity."
Jerry Colonna suggests that aggressive behavior in the venture capital industry is often a facade for underlying insecurities.
"I'm excited because it means, like, I want to support the entire entrepreneurial ecosystem."
Jerry Colonna expresses enthusiasm for the potential positive changes in the venture capital industry through self-awareness and personal growth initiatives.
"What we describe it as is to skillfully and compassionately strip away the mass so that there's no place for you to hide anymore."
Jerry Colonna describes the process of becoming authentic as a compassionate and skillful removal of the facades people hide behind.
"I think that VCs would benefit from spending more time looking at their own behavior, looking at the ways in which they are complicit in creating the conditions they say they don't want."
Jerry Colonna advises venture capitalists to reflect on their actions and the environments they contribute to creating.
"Be not afraid."
Jerry Colonna succinctly advises venture capitalists to overcome fear in their professional endeavors.
"When Things Fall Apart by Pema Chodron transformed my life."
Jerry Colonna shares a personal transformation through a book that influenced his life trajectory.
"That we all want to be a member of a tribe, that we are all afraid that we're alone, and that knowing that we're not alone creates a sense of relief."
This quote reflects Jerry Colonna's observation of a common human experience and desire for community and connection.
The key is to interview that person and really see if you have that emotional connection with them. If you can establish that rapport with that person, then the intellectual piece is easy.
This quote emphasizes the importance of emotional connection in an interview setting, suggesting that intellectual alignment follows naturally after an emotional rapport is established.
To be clear, I have worked with the same psychoanalyst for 24 years... So she's my first coach. I've also had other coaches over the years... the most important people who work with me in that way are actually my partners here at the firm.
Jerry Colonna explains that he has a consistent coaching relationship with a psychoanalyst and receives additional coaching from his business partners, highlighting the importance of continuous personal development.
Fred and Brad? Every day, mostly because it's a way to stay connected to my friends. There is one newsletter that I really enjoy. Which island of Baton's the school of life.
Jerry Colonna shares his daily reading habits and mentions a newsletter he enjoys, indicating the value he places on maintaining connections and personal growth through reading.
So I asked a couple of coaching questions... Every now and then there's going to be a little whisper in your ear, Harry, that says, but what about dating? What about friends?... What is correct is for you to keep tuning in to yourself, to those voices and saying to yourself, how's this feeling right now?
Jerry Colonna provides advice on work-life balance by encouraging introspection and listening to one's inner voice, emphasizing the personal nature of finding the right balance.
Now, I do want to say a huge thank you to Jerry for giving up his time today to come on the show... Thank you so much to him. Thank you so much to Brad Felds for making the introduction today.
Harry Stebbings expresses gratitude to Jerry Colonna for his participation and to Brad Felds for facilitating the connection, highlighting the importance of appreciation and networking in podcasting.
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