20VC Intercom Founder, Eoghan McCabe on How To Deal with the Weight of Expectation, Having Your Identity Tied To Your Company, How To Be Your Authentic Self Even with Stakeholders & Why There Are No Rules

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.

• Owen McCabe is a returning guest to the "20 minutes VC" podcast.
• He is a technology entrepreneur with a significant track record.
• McCabe's most notable venture is Intercom, a conversational relationship platform.
• As CEO, he grew Intercom to substantial revenue and a large employee base.
• He has made numerous investments in companies like Stripe and Figma.
• In 2020, McCabe transitioned to the role of chairman at Intercom.
• The host extends thanks to various individuals for their question suggestions.

"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.

• Hello Sign, an eSignature solution, found success with a user-focused product.
• Hello Sign was acquired by Dropbox after raising $16 million.
• Draper Espirit is a VC fund investing in high-growth European tech companies.
• Secureframe assists startups with SOC 2 and ISO 27001 compliance, crucial for selling to major customers.

"Check out hellosign.com 20 vc to join the thousands of companies and founders who value fast, secure and simple eSignatures."

This quote is part of an advertisement, showcasing the success of Hello Sign and promoting their service to the podcast's audience.

• McCabe's journey from Ireland to Silicon Valley embodies the classic tale of ambition.
• His passion for building, creativity, and the internet's potential led to the creation of Intercom.
• Intercom was designed to make internet business personal through messaging and bots.
• The company's mission focused on facilitating connections between online businesses and customers.

"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.

• McCabe and the host discuss the concept of having a "chip on the shoulder."
• This feeling is often rooted in a sense of inadequacy or a lack of self-love.
• Achieving external success can temporarily mask these feelings but does not resolve them.
• McCabe suggests that true fulfillment comes from internal work and self-discovery.

"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.

• The host and McCabe discuss the challenge of losing oneself in the pursuit of success.
• McCabe emphasizes that creating ego identities based on external ideals can lead to losing oneself.
• He encourages an inward journey to discover one's true self and purpose.
• The realization that happiness and wholeness come from within, not external achievements, is a pivotal point in personal growth.

"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.

• McCabe discusses the difficulty in detaching one's identity from their professional role.
• The transition from CEO to chairman at Intercom required him to redefine his sense of self.
• This detachment process is challenging due to the deep association between personal identity and professional accomplishments.

"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.

• The speaker reflects on the limitations of being defined solely by a professional title, such as "venture capitalist" or "CEO."
• They discuss the importance of recognizing one's potential beyond these titles and the rewarding experience of shedding that identity.
• The speaker shares a personal journey of moving past the CEO title and embracing a broader sense of self.

"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.

• The speaker, Owen McCabe, describes the pressure and expectations that come with the CEO title, especially as the company grows and receives more funding.
• He shares his personal approach, which involved a sense of entitlement towards investors, believing they were fortunate to be part of the company's journey.
• The speaker acknowledges the internal expectations derived from one's own insecurities and the belief of not being enough without success.

"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.

• The speaker argues that true leadership is about aligning with one's purpose and values without compromise.
• They criticize leaders who pander to popular causes without genuine commitment, which can erode trust and respect.
• Authenticity is highlighted as a key trait for building trust and respect, even if it means not pandering to every employee's desires.

"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.

• The speaker discusses the difficulty of navigating the tension between personal beliefs and the expectations of stakeholders such as VCs, LPs, and founders.
• The importance of discretion and choosing battles wisely is highlighted, with a distinction made between being authentic and unnecessarily confrontational.
• The speaker encourages speaking the truth to stakeholders, even when difficult, as a means of building genuine trust and respect.

"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.

• The speaker, Owen McCabe, expresses skepticism about the existence of fixed rules in work and life, advocating for questioning assumptions.
• They share a personal inclination towards being a contrarian and the desire to approach endeavors by asking how things can be done differently.
• The speaker suggests that value and attention gravitate towards unique and innovative approaches, rather than the mainstream.

"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.

• In the early 2010s, the prevailing belief among venture capitalists was that it was impossible to build a $100 million software business targeting small and medium-sized businesses (SMBs).
• Owen McCabe was told repeatedly that SMBs wouldn't pay enough or retain, which was seen as a barrier to significant growth.
• Despite the skepticism, McCabe and others proved this assumption wrong by successfully building large businesses, such as Mailchimp and Shopify, focused on the SMB market.
• McCabe emphasizes the importance of questioning established norms and enjoying the process of proving skeptics wrong.

"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.

• McCabe advocates for a culture that encourages questioning everything, including strategic decisions and employment practices.
• He finds it more enjoyable and fulfilling to challenge conventional wisdom and create a unique company culture.
• This approach has allowed his company to attract top talent who are drawn to the opportunity to be part of something different and innovative.

"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.

• McCabe acknowledges that while questioning everything is important, it must be balanced with structured goals, hierarchies, aggressive targets, and key performance indicators (KPIs).
• He clarifies that his company, Intercom, is an execution machine with clear structure and rigor, despite his personal advocacy for challenging the status quo.
• McCabe points out that knowing which strategic components of the business to focus on is crucial for creativity and business building.

"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.

• McCabe shares that while he tires of the minutiae of process, there is excitement in being creative on a large scale with a team of skilled professionals.
• He finds a way to balance creativity with process by partnering with individuals who can implement structure around innovation.
• McCabe's experience shows that it is possible to enjoy scaling and process when creativity is incorporated effectively.

"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.

• McCabe discusses the concept of vision, which is often celebrated in the startup world but can also be limiting if adhered to too rigidly.
• He believes that the scale of one's thinking can massively determine potential for accomplishment.
• McCabe suggests that ambition and the size of one's vision are key factors in achieving success, and that thinking bigger can lead to greater outcomes.

"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.

• Discussing the balance between being audacious and realistic when managing a fund.
• Concerns about when Limited Partners (LPs) might consider a fund size too large.
• The outcome determines if ambitions were too big or just right.
• Scale of ambition is not the problem, but rather the ability to execute.

"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.

• The importance of reading for personal development, especially during times like COVID-19 quarantine.
• A recommendation for the book "Breathe" and its impact on personal health.

"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.

• Personal tastes can reflect individual personality traits.
• The speaker identifies with a mezcal margarita cocktail for being approachable and slightly unconventional.

"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.

• Admiration for unconventional marketing strategies.
• Snapchat's vending machine marketing campaign is praised for its creativity and willingness to step outside the digital norm.

"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.

• The impact of early investors on a founder's confidence and business trajectory.
• Biz Stone's support is highlighted for its positive effect on the speaker's self-esteem and business success.

"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.

• Pride in building a successful business in a unique and personal way.
• Elon Musk is admired for his authenticity and alignment with personal values.

"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.

• The importance of authenticity and integrity in working relationships.
• Ilya Fushman is commended for his straightforwardness and lack of pretense.

"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.

• Intercom's continued growth and innovation in customer communications.
• Personal aspirations to engage in creative and fun business endeavors.

"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.

• Expressing gratitude to guests and contributors to the show.
• Encouragement to follow contributors on social media for further insights.

"I want to say huge thank you."

This common phrase shows appreciation for the guest's participation and contribution to the conversation.

• Highlighting sponsors and their contributions to the startup ecosystem.
• Mentioning companies that provide essential services for startups, such as HelloSign, Draper Esprit, and Secureframe.

"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.

"Secureframe helps startups get and maintain sock two and iso 270 zero one compliance in as little as two weeks."

Secureframe is presented as a solution for startups needing to achieve and maintain compliance with industry standards quickly.