From Startup Founder to VC: An Interview with Apostolos Papadopoulos

 

Venture Capitalists often have a background in entrepreneurship, with good reason. It is one thing to understand business theory and learn about entrepreneurship in business school. It is a whole other matter to actually have gone through the trials and tribulations of starting your own company.

It’s the difference between reading about how to do something and actually doing something. The latter teaches you far more far quicker.

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From starting his own company to working in foreign policy to now getting into venture capital, Apostolos Papadopoulos has seen it all. Born and raised in Thessaloniki, Greece, Apostolos has worked in San Francisco, New York City, London, Boston, and Vienna. Currently, Apostolos is the Biotech Expert in Residence at Greek VC Velocity Partners. That’s why for this #ThoughtImports, we thought Apostolos would be the perfect person to speak to about all things related to starting up, VC, and Greek tech.



What inspires you?

Long-term, large-scale growth. Trying to leave things a bit better for the next generation.

Contrarian, model and systems-based, heterodox and strategic thinking. The Internet. Great literature such as the classics. The Madisonian system of government and its institutions. I’m also particularly interested in Africa and China. Oh, and skiing.

Long-term, large-scale growth. Trying to leave things a bit better for the next generation.

What happened to 4sqwifi? What did you learn from it?

4sqwifi in its peak was #1 in the App Store totaling at about 200,000 and 400,000 lifetime downloads (figures are ballpark region,) launched an Android app, was covered on TechCrunch, and more. Eventually, Foursquare made some changes to its API and 4sqwifi didn’t have time to comply thus becoming effectively defunct.

4sqwifi taught me many lessons: business-wise, monetize faster and prioritize the process, especially if your users are often vocal about it. I also learned to work with and manage diverse and distributed teams, ship production software, handle media and have a media presence, how to manage a brand, how to execute. Most importantly it taught me Silicon Valley’s unwritten rule: introductions are a currency; they bind our meritocracy together.

Give liberally. Expect nothing in return. All these lessons have compounded over the years and helped me on every perceivable level.

Give liberally. Expect nothing in return. All these lessons have compounded over the years and helped me on every perceivable level.


From startup founder to now, consulting for a venture firm, can you talk about how your previous experience helps you in VC?

I think founder experience is paramount. To have had skin in the game is crucial. As a founder you’re looking for VCs that can understand you not only in terms of shared vision but in terms of the ins and outs of building the business and its culture, the hard thing about the hard things.

The added value of a VC is not just the money. There are numerous ways to raise funds for the sake of raising funds. A VC’s real value-add is the ability to mentor, help, share feedback, and best as well as worst practices. You can only teach what you know. That’s why my entrepreneurship experience was invaluable to my new role at a VC.

The added value of a VC is not just the money. There are numerous ways to raise funds for the sake of raising funds. A VC’s real value-add is the ability to mentor, help, share feedback, and best as well as worst practices. You can only teach what you know.

What do you look for when choosing ventures to invest in?

I always have a set of questions I ask myself and the founders. Some of the questions I consider—which also permeate throughout Velocity Partner’s investment philosophy—are:

  • Can this explode? What is the product hook and the distribution?

  • What is the friction to scale?

  • Is it in a boring or non-obvious space? What’s the relevant and general market?

  • Can the team solve? Can the founders attract the required talent to scale?

  • Where is the comparative advantage? What’s hard to copy?

  • Can this be a monopoly? Create and capture lasting value?

  • How this is reducing transaction costs? Can it solve the three transactions cost problem? (Trust, triangulation, transfer.)


What were some of your greatest challenges in the startup world?

If I had to sum up everything in one word it would be execution. However, if you start thinking and digging around you can dissect specific components on which “execution” builds.

These are (how to) scale, (create and maintain a great) culture, and (succeed in) hiring.

Of these three, the last two are the hardest.

What are your thoughts on Greek Tech and its future?

I’m unapologetically optimistic on a long-term scale. The community has achieved tremendous progress the past years. I’ve seen this. There’s even more room to grow now; the competition with other European hubs is even more fierce. What’s achieved so far can’t go unacknowledged. Call me crazy, but if some systemic things change in the future (from business environment to the university - research - job marketplace nexus of connections) we are set to see even greater things happening. Entrepreneurs are thirsty for less roadblocks.

I’m unapologetically optimistic (about Greek tech) on a long-term scale.

What are some pieces of advice you have for greek entrepreneurs?

In answering this I want to initially echo my friend and prolific founder Nick Papanotas: just build the darn thing. Build, execute, ship. Significant parts of the tech stack have been completely commoditized to the point it’s extremely easily to set up anything from anywhere in the world—even payments. It’s easy to experiment and challenge your assumptions.

It’s easy to experiment and challenge your assumptions.

Still, from a pure utilitarian point of view, with the minimal amount of friction which exists nowadays to ship, it’s come to the fact that you’re potentially depriving society of an improvement—however marginal or on the sides—if you don’t ship. Lastly, don’t think in terms of the Greek or European market.

What does every pitch deck need to have? What will make it stand out?

A story and a message that underscore and enhance the founders’ vision, as well as a coherent template (ranging from typography to colors to text size and structure.) One might easily dismiss its significance, but the devil is in the details—and I’m a stickler for the details. Attention to detail and ability to tell a story are crucial.

Do you think you’ll want to start your own company again in the future?

I’m not known for saying no to good opportunities.


Key Takeaways for Business and Life

  1. Give liberally. Expect nothing in return. In the business world and in life, givers succeed. How? Check out Adam Grant’s Ted Talk on how to be a successful giver.

  2. To have skin in the game is crucial. As Nicholas Nassim Taleb writes in his book of the same name, “the knowledge we get by tinkering, via trial and error, experience, and the workings of time, in other words, contact with the earth, is vastly superior to that obtained through reasoning.” Having entrepreneurship experience makes you a much better investor and advisor.

  3. If you’re not embarrassed by what you ship, then you’ve waited too long. Just ship the product. The mentality of testing an imperfect product in the market and learning from customer feedback is one that is completely and utterly terrifying to entrepreneurs. You have nurtured their idea for years, pouring your blood, sweat, and tears into it. Thus, sending out something that is anything less than perfect to the market is terrifying. However this is the best possible thing that you can do for the success of your company.

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Comments or questions on starting up, #Greektech, or anything else? We’d love to hear from you! Leave us a note in the comments below, or shoot us an email: sail@totheport.com.