20VC CEO Whisperer Jerry Colonna on How Investors Mimic Aggressive Behaviour To Cover Insecurity and Why Vulnerability is Key To Success In VC

Summary Notes


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.

Summary Notes

Introduction to the Podcast

  • Harry Stebbings introduces the 20 minutes VC podcast episode.
  • This episode is described as very different, real, deep, and thought-provoking for Founders Friday.
  • Harry Stebbings can be added on Snapchat.

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.

Guest Introduction: Jerry Colonna

  • Jerry Colonna is introduced as the episode's guest.
  • He is known as the CEO Whisperer and is a founder at Reboot.
  • Reboot is a coaching company that supports entrepreneurs and investors with internal challenges.
  • Jerry's background includes being a partner at JPMorgan and a VC at Flatiron Partners.
  • Flatiron Partners was successful with investments in companies like Geocities and New York Times Digital.
  • Harry Stebbings mentions a personal application of Jerry's advice to be real and true to oneself.

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.

  • Harry Stebbings talks about Luma, a surround Wi-Fi system.
  • He shares his personal experience with Luma, describing the improvement in his home Wi-Fi.
  • Luma's ease of setup and network management is highlighted.
  • Listeners are directed to various outlets where they can purchase Luma.

Now, for those that don't know, Luma is the world's first ever surround Wi-Fi system. And before I had Luma man, the Wi-Fi in my house sucked. It's a tool townhouse, and there are always blind spots. So I got Luma, and it came with three routers. I placed one in the living room, one in the kitchen, and one on the top floor. The setup was super simple. I think it took me less than ten minutes to do all three routers and then download the app as well. Now I can see who is on my network, what they're doing on the network, and also people can do a ton with the network itself.

This quote provides a testimonial for Luma, emphasizing its benefits and encouraging listeners to consider purchasing it.

Jerry's Early Career and Entry into Venture Capital

  • Jerry Colonna shares his journey into venture capital (VC).
  • He started as a technology reporter and editor before moving into VC.
  • Jerry's early recognition of the web's potential led to launching magazines online.
  • He joined CMG at Ventures, focusing on Internet-based investments.
  • Jerry later co-founded Flatiron Partners with Fred Wilson in 1996.

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.

Transition to Coaching and the Creation of Reboot

  • Jerry Colonna discusses his transition from VC to coaching.
  • The shift was influenced by a profound existential depression he experienced.
  • Jerry openly shares his past struggles with depression and a suicidal attempt.
  • His personal challenges led him to focus on mental health and eventually to coaching.

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.

Career Transition and Discovery of Coaching

  • Jerry Colonna discusses his painful departure from his partnership with Fred, despite their close friendship.
  • He joined J.P. Morgan, but soon realized it was not the right fit for him.
  • Jerry spent years in existential exploration after leaving J.P. Morgan at the end of his contract.
  • The transition to coaching began as he was figuring out his life during this period.
  • Jerry discovered his coaching ability when he asked a young attorney why he chose a profession he hated, leading to an emotional reaction.

"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.

Radical Self-Inquiry and Unconscious Motivations

  • Jerry Colonna emphasizes that making the unconscious conscious is an ongoing process, not a one-time event.
  • He experienced a moment of clarity when he felt a strong internal push towards coaching.
  • This realization was accompanied by physical sensations and emotional intensity, indicating a deep connection to his true self.

"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.

Work-Life Integration vs. Compartmentalization

  • Jerry Colonna discusses the concept of compartmentalization as a coping mechanism to manage daily life.
  • He warns against the prolonged disconnection between one's inner reality and external persona, which can lead to depression.
  • Jerry advocates for work-life integration, where personal values and professional environments align, leading to fulfillment and energy rather than suffering.

"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.

Embracing Vulnerability in Professional Environments

  • Jerry Colonna discusses the importance of vulnerability in the workplace and its impact on personal well-being.
  • He mentions Fred Wilson's blog post about the value of caring in the venture capital industry, challenging the traditional business playbook.
  • Jerry encourages entrepreneurs and professionals to embrace their true selves, regardless of industry norms.

"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.

Authenticity in Professional Life

  • The pressure to conform to others' expectations can lead to a loss of self.
  • Pretending to care or to be tough masks true emotions and can be harmful.
  • Venture capitalists often exhibit aggressive behavior to cover insecurities, primarily the fear of losing money and being labeled as a poor investor.

"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.

Venture Capitalist Self-Integration

  • Excitement about the venture ecosystem's openness to personal growth and self-integration.
  • The success of VC boot camps indicates a shift in the industry towards self-awareness.
  • The current method of operating in venture capital may not lead to better returns and can be painful.

"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.

The Path to Authenticity

  • The first step to authenticity is self-examination and acknowledgment of one's true self.
  • It involves stripping away masks and confronting personal baggage.

"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.

VC's Self-Reflection on Impact

  • VCs should spend more time understanding their behavior and its impact on others.
  • Reflection on why certain investments are made repeatedly can reveal unconscious patterns.

"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.

Advice to Venture Capitalists

  • The essential advice to VCs is to not be afraid in various aspects of their professional life.
  • Embracing fearlessness can improve relationships with founders, investment decisions, and overall handling of business relationships.

"Be not afraid."

Jerry Colonna succinctly advises venture capitalists to overcome fear in their professional endeavors.

Quick-Fire Responses

  • Favorite books: "When Things Fall Apart" by Pema Chodron and "Let Your Life Speak" by Parker Palmer, both of which significantly impacted Jerry Colonna's life in 2002.
  • The biggest takeaway from running boot camps is the universal desire to belong and the relief in knowing we are not alone.
  • Finding a mentor involves speaking to others about who has been helpful to them.

"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.

Emotional Connection in Interviews

  • Establishing emotional rapport is crucial in interviews.
  • Intellectual compatibility is easier to achieve once emotional connection is established.

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.

Coaching for Coaches

  • Jerry Colonna has a long-term relationship with a psychoanalyst who acts as his coach.
  • Jerry also relies on his partners at his firm for coaching.
  • The firm's values are aligned with the inner and outer aspects of life, and they practice this through active collaboration.
  • Coaching is integrated into the company culture and demonstrated in their bootcamp.

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.

Reading Habits

  • Jerry reads Fred and Brad's writings daily to stay connected with friends.
  • He enjoys the newsletter from the School of Life.

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.

Work-Life Balance Advice

  • Jerry advises tuning in to one's feelings about work-life balance.
  • He questions the notion of happiness in relation to work, especially for someone who prioritizes work above all else.
  • Jerry encourages reflection on personal satisfaction and the importance of other life aspects like relationships and health.

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.

Show Appreciation and Networking

  • Thanks are given to Jerry Colonna for his time and insights.
  • Acknowledgment of Brad Felds for the introduction.
  • Invitation to follow the podcast on Snapchat and sign up for the newsletter.

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.

Product Promotion

  • Luma is promoted as a solution for Wi-Fi needs in various home scenarios.
  • The product offers speed, security, and control over the home network.
  • Luma devices work together to create a mesh network with an easy setup guided by an app.

Luma is the world's first ever surround Wi-Fi system... Luma's app lets you easily see and control which devices, users, and content are being used on your network.

Harry Stebbings advertises Luma as an innovative Wi-Fi system that enhances home internet experiences, demonstrating the integration of product promotion within podcast content.

What others are sharing

Go To Library

Want to Deciphr in private?
- It's completely free

Deciphr Now
Footer background
Crossed lines icon
Crossed lines icon
Crossed lines icon
Crossed lines icon
Crossed lines icon
Crossed lines icon
Crossed lines icon

© 2024 Deciphr

Terms and ConditionsPrivacy Policy