In a thought-provoking conversation on "20 minutes VC," Harry Stebbings reconnects with Owen McCabe, the esteemed technology entrepreneur and chairman of Intercom. McCabe shares insights from his journey, including the growth of Intercom into a multi-million dollar business and his transition to chairman. The dialogue delves into themes of self-worth, the illusion of external validation, and the importance of internal work and self-discovery. McCabe emphasizes the power of thinking big and the need for authenticity in leadership, advocating for leaders to stand by their values and question industry norms. He also touches on the balance between creativity and process in scaling businesses. The discussion concludes with McCabe's future aspirations, hinting at more innovative ventures ahead.
"I'm thrilled to welcome back to the hot seat Owen McCabe, a technology entrepreneur who has started a number of companies, the most notable of which Intercom, the conversational relationship platform."
This quote introduces Owen McCabe and highlights his achievements, providing context for the conversation and setting up the significance of his insights.
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This quote is part of an advertisement, showcasing the success of Hello Sign and promoting their service to the podcast's audience.
"Our mission was to make Internet business personal. And we made this little messenger and then bots that let these online companies and their customers really get to know each other and get their work done."
This quote explains the core mission of Intercom and how it aimed to transform the way online businesses interact with customers.
"It means you think there's something lacking in you. It's a lack of self-love. It's a sense that you're not good enough and that you need to possess or achieve something to be lovable or popular or safe or whatever."
This quote delves into the psychological aspect of ambition, describing the "chip on the shoulder" as a deeper issue of self-perception and the need for internal validation.
"You kind of have to go that journey. You kind of have to prove yourself wrong before you can do the harder work."
This quote underscores the importance of self-exploration and the realization that external accomplishments do not equate to internal fulfillment.
"We've worked so hard because we believe that they are the thing we need, that they are us."
This quote reflects on the struggle to separate personal identity from one's professional achievements and the importance of recognizing oneself beyond these roles.
"When I thought I was a CEO, I was trapped by that. Even though I knew I had so many more things I wanted to do with my life and ways, I want to invest my energy and different missions and adventures."
This quote illustrates the speaker's realization that identifying solely with a job title can be limiting and that there is value in pursuing a more expansive self-concept.
"I didn't really feel expectation in that respect. I felt expectation from myself."
This quote emphasizes that the speaker's main source of pressure was self-imposed, stemming from a deep-seated belief of personal inadequacy rather than external expectations from investors.
"I think that real leadership equates to a deep connection with your purpose and your values, and any deviation from that makes for a bad leader and poor leadership."
This quote captures the speaker's belief that true leadership is rooted in staying true to one's core values and purpose, rather than pandering to the crowd.
"It's easier said than done. My co-founder Des used to say, discretion is the greater part of valor."
This quote reflects the idea that while it's challenging, exercising discretion and being selective about when to express opinions is a valuable skill for maintaining authenticity without causing undue conflict.
"I don't believe that there are any rules in work and life. I have always taken a healthy approach to any endeavor where I try and question all the assumptions."
This quote highlights the speaker's philosophy of challenging the status quo and seeking out original and distinctive paths in both professional and personal endeavors.
"I was told, and all the way into 2013, actually, when I was raising our series a, I was told, you cannot build 100 million dollar software business selling to SMB."
This quote highlights the skepticism Owen McCabe faced from venture capitalists about the potential of the SMB market for significant business growth.
"We built 100 million dollar business with SMB."
McCabe refutes the earlier skepticism by stating the success of his business, which was built by targeting SMBs, demonstrating the flawed nature of the prevailing belief.
"Rip up the rules, surprise people. The degree to which you can inspire and ignite an imagination and make people so proud to be part of a company that is different is quite shocking."
This quote illustrates McCabe's philosophy of breaking the norm to inspire and attract individuals who want to be part of a unique and creative company culture.
"We question everything, but we have structure and rigor and process."
This quote emphasizes that despite the culture of questioning, there is a strong foundation of structure and process in place at Intercom, ensuring effective execution.
"It can be super fun to be creative on a big scale."
McCabe expresses how creativity can be thrilling even as a company grows and scales, suggesting that large-scale innovation can be enjoyable.
"Vision happens whether you like it or not. Vision is just how you think about the future."
This quote explains that vision is an inherent part of planning for the future and is not necessarily grandiose but varies in scope.
"The scale of your thinking is everything. Just think bigger, bigger, bigger, bigger."
McCabe encourages expansive thinking, implying that larger visions can lead to greater achievements and should not be underestimated.
"The answer is in the outcome. Those who had the big ambitions and pulled it off, well, it turns out that they weren't thinking too big. Those that did and didn't, they were."
This quote emphasizes that the success of an ambitious venture is what validates the scale of the ambition. If the venture succeeds, the ambition wasn't too big; if it fails, it may have been too large.
"I don't think there's any answer, but I don't think the scale of their ambition was the problem. I think it was their ability to meet that and to execute."
The quote suggests that the issue with ambitious ventures is not the ambition itself but the entrepreneurs' capacity to realize those ambitions.
"It's not that anyone thinks too big. It's that some people think wrong."
This quote implies that the problem is not with the size of the ideas but with the appropriateness and practicality of the ideas in relation to the individual's capabilities or the reality of the business environment.
"It's called breathe. And it will convince you that you have been breathing wrong your whole life."
This quote highlights a current reading choice that has influenced the speaker's daily habits, suggesting the book offers valuable insights into a fundamental aspect of health.
"I like mezcal margaritas, and I think that works for me because it's kind of approachable to everyone. It's got something for everyone, but it's also got a little twist with the mezcal."
The quote reveals the speaker's self-perception as being inclusive yet distinctive, much like their preferred cocktail.
"I just love that they decided to be weird."
This quote appreciates Snapchat's marketing campaign for its uniqueness and departure from typical digital marketing strategies.
"For a young lad in this big industry who really thought very little of himself, to have someone so accomplished simply give you the time of day and treat you like you're important, like he always did, boosted my confidence no end."
The speaker attributes a significant boost in confidence to the support and recognition from an accomplished investor, which underscores the importance of mentorship in entrepreneurship.
"It's building a multibillion dollar, many hundreds of millions of dollars in revenue business my way, doing it in a silly, playful, creative, loving fashion that no one did before by ripping up the rules and figuring out that that works, too."
This quote reflects a sense of achievement in creating a successful business while maintaining a playful and creative approach, defying conventional wisdom.
"I really admire the guy. He's no less than my hero these days."
The speaker expresses admiration for Elon Musk, highlighting him as a personal hero and role model.
"I'm a stickler for integrity and authenticity, and Ilya was what he was and is what he is. And there was no games."
The speaker values genuine interactions and straightforwardness, which Ilya Fushman exemplified, making him a respected board member.
"We continue to dominate the space of customer communications and no less and revolutionize how online business is done."
This quote outlines Intercom's ambition to remain a leader in customer communications and to innovate in the online business space.
"I have a lot of businesses and different ideas still in me and there's different things I've been thinking about for some time."
The speaker shares a desire to explore various business ideas and maintain a playful and creative approach to entrepreneurship.
"I want to say huge thank you."
This common phrase shows appreciation for the guest's participation and contribution to the conversation.
"Hello Sign is an effortless esignature solution used by millions to securely send and request legally valid digital signatures and agreements."
This quote introduces HelloSign as a valuable tool for startups, emphasizing its ease of use and security features.
"Draper Esprit, a publicly listed VC fund that invests in high growth european tech companies with global ambitions."
The speaker promotes Draper Esprit as a significant venture capital fund supporting high-growth companies in Europe.
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