Aug 24 • 39M

Super Angel #206 Manolis Manassakis, Qogita & Cloud Nine Ventures

Read on for the core insights 👀 From Google, Uber and founding Lawspot to leading Qogita and Cloud Nine Ventures, Manolis is an angel worth paying attention to.

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Today, Anthony and I are happy to welcome you to Manolis Manassakis, CEO of Qogita, a leading global wholesale supplier revolutionizing the market through technology.

Manolis was formerly the Director of Operations for Europe, Middle East and Africa at Uber. Earlier in his career, he worked at Google as an Industry Manager, helping European businesses boost their online sales and make the most out of the web. Parallel to his work, Manolis co-founded Lawspot, providing openness and transparency to the law, to all citizens. Lawspot is now Greece's no1 open online hub for all things legal, trusted by 1M monthly users.

Through Cloud Nine Ventures, Manolis is also an active angel investor, passionate about the European tech ecosystem, and loves helping startups and mentoring founders on operations, scaling and international expansion. While this may sound like a mere side gig, Manolis has built a brand and respect in the angel ecosystem that places him amongst titans of Greek venture.

Core Learnings and Insights from the Conversation:

1. Strategic Simplicity Over Overcomplication: Manolis emphasizes the allure of fundamental principles over excessive complexity. He challenges the prevailing trend of overcomplicating investment decisions with extensive documentation, highlighting that success isn't guaranteed by the length of an investment memo.

2. The "Right to Win" Framework: Cloud Nine Ventures' investment philosophy centers around the "right to win." This concept examines four key dimensions: the team's competence, the unique angle of the venture, the potential for disruption in the space, and the timing of entry.

3. Caution in the "Why Now?" Question: While recognizing the importance of the "Why now?" question, Manolis advocates for a nuanced approach. He prefers less obvious and more enduring reasons behind a startup's timing, grounded in concrete industry dynamics rather than fleeting trends.

4. Quality-Centric Diversification: Cloud Nine Ventures favors quality over quantity when it comes to investment diversification. Rather than making numerous investments, they focus on maximizing the impact of each investment, leveraging the diverse skill sets of their partners to provide substantial support.

5. Angel Investing Collaboration: The collaborative structure of Cloud Nine Ventures, with partners possessing diverse expertise, amplifies their ability to support startups. The combination of complementary skills offers founders a conglomerate of insights and guidance.

6. The Power of Attentive Listening: Manolis highlights the significance of active listening, underscoring that a single word or phrase can hold immense influence. This skill is vital for understanding nuances in conversations and uncovering key insights.

7. Uniqueness in Execution: Execution strategies are nuanced and unique to each business. Manolis's example of Airbnb's breakthrough emphasizes the importance of understanding minute details that can profoundly impact a venture's success.

8. Cautious Approach to "Why Now?": "Why now?" should be examined carefully, avoiding herd mentality and embracing deeper industry trends. Understanding the distinct reasons behind a venture's timing is crucial for long-term success.

9. The Uncertainty of Success and Happiness: Manolis advises embracing uncertainty, acknowledging that many aspects of life and business are balanced between success and the opposite. It's essential to recognize the unpredictability and allow for happenstance to play a role.

10. Multifaceted Contributions: Manolis's journey showcases the possibility of multifaceted contributions. From corporate leadership to entrepreneurial ventures to angel investing, his varied roles demonstrate the potential for impacting different aspects of the business ecosystem.

11. Empowerment Through Innovation: Beyond corporate endeavors, Manolis's commitment to empowerment is evident in ventures like Lawspot. His dedication to knowledge dissemination showcases the potential for businesses to create positive change.

12. Value of Niche Expertise: Manolis's expertise lies in delving into deeper, less obvious areas. His preference for "heavier" spaces and enduring trends demonstrates the value of niche expertise over following trendy waves.

13. Collaborative Investment Networks: The mechanics of investment networks, or syndicates, involve shared investment opportunities and connections. These networks leverage the expertise of company alumni, facilitating support and growth for startups.

14. Unanticipated Investment Success: Manolis's investment journey includes instances where initial uncertainty led to significant success. The tale of a surprising Middle Eastern investment highlights the art of calculated risk-taking and the potential for unexpected growth.

15. Entrepreneurial Philosophy: Manolis's philosophy revolves around depth, specificity, and a willingness to challenge conventions. His insights offer a roadmap for investors and innovators seeking to achieve success by understanding the nuances and intricacies of each venture.

Read on to dive deeper ⏬ and watch the conversation in full 👀

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Manolis’ Journey Into Angel Investing

With a journey that traces back to his roots as a lawyer, Manolis's venture into the realm of technology and angel investing is a tale of transformation, innovation, and calculated risk-taking.

A Trailblazing Odyssey: From Corporate Heights to Entrepreneurial Spirit

Manolis Manassakis, a name synonymous with innovation, brings a remarkable resume adorned with pivotal roles and impactful ventures. From his role as the Director of Operations for Europe, Middle East, and Africa at Uber, where his strategic prowess reshaped regional growth, to his inception at Google as an Industry Manager, catalyzing online sales for European businesses, Manolis's journey is one of strategic brilliance.

Pioneering Spirit: Empowering Through Innovation

Yet, beyond the corporate realm, Manolis's commitment to empowerment shines even brighter. A co-founder of Lawspot, he championed transparency in the legal landscape, crafting Greece's premier open online hub for legal matters. His devotion to knowledge and accessibility transcends business, resonating with every citizen seeking legal clarity.

Cloud Nine Ventures: A Confluence of Vision and Mentorship

Venturing beyond the conventional, Manolis's role as a founding partner at Cloud Nine Ventures is a testament to his dedication to the European tech ecosystem. As an angel investor, he not only provides financial backing but actively nurtures startups, lending his expertise in operations, scaling, and international expansion.

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Manolis’ Investment Thesis & Strategy

Stripping Away the Illusion of Complexity

Manolis begins by questioning a prevailing trend in the investment landscape—a perceived overcomplication that beclouds the decision-making process. Drawing parallels across diverse asset classes, he highlights the allure of an intricately detailed investment memo, an overwrought attempt to mitigate the anxiety of making a misstep.

💡 Insight
Manolis urges a return to fundamental principles, a reminder that a lengthier memo doesn't necessarily guarantee success, nor does it eliminate risk.

Unpacking the Essence: The Right to Win

Stepping into the core of Cloud Nine Ventures' investment philosophy, Manolis lays bare the driving force behind their discerning choices—the concept of the "right to win." A succinct question takes center stage: What sets this team apart, granting them the undeniable right to triumph? Manolis distills this assessment into four pivotal dimensions:

  1. The Team: Paramount, especially in the early stages when historical traction might be limited. The team's competence, cohesion, and adaptability hold the key to success.

  2. The Angle: How does the venture strategically position itself within its chosen domain? This angle serves as a unique differentiator that can tip the scales in favor of success.

  3. The Space: The broader market landscape. Is the venture operating in a space with room for innovation and disruption, or one saturated with imitations and incremental changes?

  4. The Time: A delicate balance. While the "Why now?" factor can lead to opportunistic thinking, focusing on enduring trends rather than transient fads can yield more consistent results.

A Nuanced Approach to Timing

Manolis casts a spotlight on the "Why now?" question, a cornerstone of early-stage evaluation. While acknowledging its relevance, he voices caution against unwavering adherence. He champions a deeper dive into what he terms "heavier spaces," areas less swayed by fleeting trends. This stance ensures a more robust foundation and a reduced likelihood of opportunism clouding judgment.

Diversification: A Deliberate Approach

Moving to the thorny issue of diversification, Manolis introduces a refreshing counterpoint to conventional wisdom. While the volume approach—often championed by VC firms—can yield results, Cloud Nine Ventures embraces a different ethos. Their approach is quality-centric, favoring in-depth support over a sheer number of investments. Manolis acknowledges that their strategy may not fit the profile of certain LPs seeking a broader spread. Instead, Cloud Nine Ventures consciously maximizes the impact of each investment, bolstered by the diverse skill sets of its partners.

A Quintessential Collaboration: Cloud Nine's Distinct Edge

Manolis's discussion culminates with a reflection on Cloud Nine Ventures' distinctive composition. The diverse backgrounds of its partners—spanning finance, operations, tech, and more—lend a multidimensional support system to startups. With this array of expertise, a single investment brings forth a conglomerate of insights and guidance, elevating the level of hands-on involvement.

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Manolis’ Core Learnings from Angel Investing

With a penchant for candid introspection, Manolis touches upon key areas that have marked his journey and shaped his perspective, offering a rare glimpse into the mindset of an accomplished entrepreneur and investor.

The Art of Attentive Listening

Manolis begins with a revelation that reverberates with honesty: the pursuit of becoming a better listener. Acknowledging his natural inclination to express ideas, he recognizes the pivotal role of listening—a cultural element that transcends communication. He underscores the significance of a single word, a brief phrase, or a succinct sentence that can wield immeasurable influence. It's a reminder that beneath the complexity of discourse, the essence often lies in the minimalist, the nuanced.

Unraveling the Tapestry of Uniqueness in Execution

Diving deeper, Manolis unveils the enigma of execution—a realm that defies generic templates. While acknowledging the gleanable insights and learnings from podcasts and discussions, he discerns the profound uniqueness that underpins execution strategies. Manolis alludes to the intricate dance of marketplaces, where solutions to challenges like the chicken-and-egg problem demand a profound depth of understanding. He shares a resonant anecdote—the Airbnb breakthrough. Here, the key lay not in grand strategies, but in a seemingly minor detail: the quality of photos. The revelation lies in understanding the idiosyncrasies of each startup you meet and crafting strategies that resonate with its essence.

Beyond the Obvious: Unveiling the "Why Now?"

The conversation traverses to the intriguing concept of "Why now?" This seemingly simple question embodies layers of complexity that can shape the destiny of startups. Manolis issues a word of caution, urging founders and investors alike to tread carefully. While acknowledging the allure of trends and herd mentality, he champions the value of delving deeper. He highlights his preference for less glamorous, less evident "Why now?" factors. These factors, anchored in the concrete rather than the ethereal, often spell the difference between enduring success and fleeting trends. Manolis's wisdom echoes; True understanding of the "Why now?"-question is the culmination of deep expertise and contextual awareness.

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🔫 The Quickfire Round 🔫

Q: What's the most counterintuitive lesson you've learned from your angel investing experience?

 I've found myself inclined to trust introverted founders more than extroverted ones, despite my own extroverted nature. Sometimes, extroverts come off as overly focused on sales and lacking in data-driven approaches—unfairly and justly so. It's a personal bias on my part, my mistake. I tend to place my trust in founders who are less flashy, less focused on sales, and more driven by concise, data-backed insights.

Q: What's your top tip for Angels looking to venture into international investments?

 Go for a walk and question whether your interest in international investments is genuine or if it's just a trendy facade to enhance your image.

Q: If you could offer one piece of advice to your younger self in just 30 seconds, what would it be?

Stress way less. You often don't have a clear understanding of what's truly beneficial for you. Numerous times I wished for something and didn't attain it, only to later realize it was for the best. The opposite has also proven true. This isn't confined to the professional sphere. It's not about being romantic or seeking self-help solutions, just pure rationality. Many things are split down the middle—50% leading to success or happiness, and 50% leading elsewhere. Embrace the role of chance because the reality is, you frequently lack all the answers.

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