Startup. Exit. Repeat.
Journey of a second-time founder
Today’s post marks the fifth anniversary of Startup Pirate. This is edition #118, and I couldn’t be more grateful to all of you who’ve tagged along on this journey. A lot has changed since April 2020 (edition #1 was very much focused on health tech startups leading covid lockdown initiatives), yet my thesis remains: Surface stories of Greeks in tech building cool things and pushing frontiers.
As I previously wrote in this piece, rebellion, creativity, and risk-taking are culturally ingrained. It’s watching your peers venture and succeed or fail. Startups cannot be taught nor cultivated through tax credits & non-dilutive grants. If this newsletter helps at least a handful of people connect the dots and go build or join the craziest, most ambitious startups, I’m happy :)
Let's roll on to the decade milestone. If you’re not a subscriber, hit the button below and come aboard 🏴☠️
Startup. Exit. Repeat.
The following is a conversation with Conno Christou, co-founder & CEO of Keragon, a workflow automation platform for the healthcare industry. Conno previously co-founded Avocarrot, an ad tech company acquired by Glispa Global Group in 2016 for $20 million. Conno shared his fascinating journey building startups since 2012:
Why ad tech was broken in the early 2010s and the start of Avocarrot
Getting acquired by a prominent ad tech company
Persuading the acquirer to double down on the Athens office
From ads to healthcare, and founding Keragon
Fundraising and hiring as a repeat founder
Missing the raw energy and naive optimism of a first-time founder
AI as the game changer for team productivity
Let’s get to it.
Alex: Conno, it's fantastic to see you and the rest of the Avocarrot founding team back in building mode. Correct me if I'm wrong… You have known each other for 20 years, and your story hacking together started with a fashion application in 2012?
Conno: Oh, my days - that’s ancient history now! With George Eracleous, George Makkoulis, and Panos Papageorgiou, we all served in the military together in Cyprus, then attended the same university in London, and after graduating in 2012, we started going to hackathons and building stuff.
At some point, we developed a fashion application that allowed users to share photos of clothes they wanted to buy, and their friends could vote with a thumbs up or down. With that prototype, we won the London Hackathon. We explored ways to make money from this and realised mobile advertising was clunky, intrusive, and not optimised for user experience. We decided to build an advertising platform prioritising the UX on the app developer side - a novel idea for the early 2010s. Facebook and Instagram started serving native mobile ads 1-2 years after us. The aha moment was when we realised that click-through rates were 15x-20x higher than incumbent solutions; hence, we went all in on developing that technology. That's how Avocarrot was born. We got some small funding, which gave us runway for a few months while building the beta version across London and San Francisco.
Alex: Fast forward to 2016, when advertising tech company Glispa acquired you. How did that acquisition come about?
Conno: Throughout those years, we had built an ad exchange with an emphasis on the UX and the look and feel of the ad, while developing a real-time bidding engine in the background. This allowed advertisers to bid on that inventory and get in front of the right people at the right time, as we had gathered tons of user metadata. Around that time, we were live on 10,000 apps worldwide, serving approximately 4 billion ads per month. Our network and technology were valuable for larger players such as Glispa, which eventually acquired us in 2016. They were very bullish on our team, our tech, and the timing.
Alex: At that time, most of your engineering team was based in Athens. We have observed several instances where local teams remain flat or gradually fade after the acquisition. But that was not the case with you. Does it always come down to winning the internal politics game, and what were the main arguments for doubling down in Greece?
Conno: Moving to Greece to build the company was one of our best decisions. At some point in late 2013, we had to move back to Cyprus because the company was running out of money. Both London and San Francisco were very expensive cities to live in, and we still hadn’t raised that $2 million Seed round. After a few months of interviews, we decided to review more candidates for our team, so we ran parallel interviews in both Cyprus and Greece. We had our first exceptional hiring interview in Athens, and hence we decided to relocate there. This eventually worked out wonders. When Glispa acquired us, we were a team of 17, most of us based in Athens.
Company politics is a big part of the game. Our main negotiating power was one thing: always over-deliver. Since the early days of the acquisition, we have been continuously shipping features, driving revenue, and building trust. After Avocarrot, Glispa acquired another six or seven companies, while the leadership team continued to bring these products under our umbrella. Imagine the leverage we had by leading all of them. That was the primary driver for convincing Glispa to invest further in local engineering talent. Three years later, we were a team of 50 strong engineers in Athens.
Alex: How long did you stay around after the acquisition?
Conno: 3 years, 8 months, and 17 days.
Alex: You were really counting down the days, weren’t you? What drew you to healthcare and Keragon?
Conno: It took us a while to jump into another idea. All four of us left Glispa at the same time and took some time off to recharge and think of our next steps. That break lasted for about two years. Healthcare drew our attention early in our brainstorming for the following reasons: a. It’s a space we can positively influence people's lives, even indirectly, b. We believe healthcare is ripe for disruption in the next 5-10 years, and we wanted to ride that wave.
With Keragon, we are building the "Zapier for healthcare". We integrate with the most widely used healthcare vendors, enabling our clients - the doctors - to set up automations across different tools without needing code. Right after COVID, the healthcare industry was pushed to go digital, and a lot of VC money chased startups creating best-of-breed solutions for each part of the operation: scheduling, CRMs, patient intake forms, engagement platforms, etc. However, as of today, these platforms don’t connect with each other. Doctors typically use a dozen siloed new digital tools on average. Moreover, there's a shortage of 30,000 doctors in the US alone. Imagine how overworked they are. There's a lot of burnout and turnover. It's a mess. That's why we came in.
Currently, this problem is very acute, and the opportunity is huge. We solve this by providing a very intuitive platform with a no-code editor, for anyone to drag and drop the tools they use and set up workflows in an "if this, then that" manner. You set it up once, and it's automated from then on. The nuance here is that compliance, security, and reliability are of the utmost importance in healthcare. You are not automating just a Slack notification - these are patient workflows, in most cases clinical/critical operations for healthcare organisations. You need to be reliable, secure and compliant at scale. That’s why we chose to keep a low profile for two years before our public launch, to build internal confidence in these three critical pillars. The threshold for an MVP with Keragon was much higher than placing ads in mobile apps.
Alex: I want to switch gears and take you to company building, and specifically, go-to-market, as a second-time founder. I often think about the tweet below by Justin Kan, the founder of Twitch. Do you agree, and is it how you approach things now with Keragon?
Conno: Ha, first time I hear this - there’s definitely some truth to it. In our case, even though we’re still kind of obsessed with product, we now actively think about how distribution can be embedded directly into the product experience. That means being intentional about how new users find us, how word spreads, and how we reduce friction to adoption.
It’s a bit unusual in healthcare, where services often take the lead. But all four of us come from the tech world, so for better or worse, we naturally approach things through a product-first lens - even when we’re thinking about growth.
Alex: I'm curious to hear what you've done differently with fundraising and hiring this time with Keragon.
Conno: We are more deliberate now. Sure, being second-time founders with an exit under our belts made things easier for us. We raised our first round when we had enough conviction that this idea was worth pursuing. We were new to the space, so we initially took enough time to talk to potential customers, explore the healthcare technology ecosystem, and develop an early version of Keragon. We didn't go out to raise funding on day 1.
On top of that, we only contacted investors we thought would be a great match based on their experience and thesis. Since we’re new to the healthcare space, we sought to partner with someone who has a deep understanding of healthcare to complement our product and technical backgrounds. We have raised two rounds: $3 million and then $7.5 million, following initial customer traction. As everybody says, good traction makes everybody want to work with you. In later rounds (Series A+), the second-time founder effect diminishes as you’re now raising on a spreadsheet, not on a deck.
Hiring was one of the things we learned a ton about while building Avocarrot. We have always been ruthless about candidate fit, using three pillars to determine this: people who are smart, get things done, and have the right cultural fit. A candidate must tick all three boxes to be hired. We are fortunate to have worked with some fantastic individuals in our previous company, which provided us with a significant boost in the early days of Keragon as we joined forces with a few of them again.
Alex: There’s data to back up that second-time founders are often far more equipped to succeed than their inexperienced earlier selves. However, I want to turn the argument around. What are the “benefits” of first-time founders?
Conno: First-timers often possess raw energy and naive optimism, which are great traits for founders. There's magic in not knowing what's impossible! They jump in with fresh eyes. They may have heard about how challenging it is to build a company, but they don't truly know. First-time founders lack painful memories that introduce hesitation. And it's the lack of fear of failure that empowers them to pursue bold new ideas.
In contrast, second-time founders have experienced the ups and downs of their first startup and are aware of the risks and challenges. They have scars that can introduce hesitation, so they make excuses not to pursue something new, which is partly why it took us so long to decide on our next startup idea. Analysis turns into paralysis… On our end, we wanted to "hack" that naivety, therefore, we decided to venture into a new sector: healthcare. While brainstorming for new startup ideas, we had a very important rule: anything but ad tech.
Alex: We talked offline about this before… You are a strong proponent of using AI internally at Keragon to boost your team's productivity. I'd love to share your thesis about that. For context, I'm also attaching the recent memo from Shopify, pulling some quotes from it: "Using AI effectively is now a fundamental expectation of everyone at Shopify", or "Before asking for more headcount and resources, teams must demonstrate why they cannot get what they want done using AI".
Conno: We continuously try to find ways to 10x the productivity of our team. We are reshaping the company through processes and projects to force us to adopt AI tools and become an AI-first company. This Shopify memo is spot on. We know we are leaving a lot of optimisation on the table, and it's something we are doubling down on. It's actually one of our company's five core values: If you find yourself doing something manual twice, automate it. We always think about automation with AI at the core. We believe we can be 10x more productive using automations and AI. We’re an automations company after all..
Alex: You mentioned five core company values, so I have to ask… What are the other four, apart from automate things?
Conno: a. Over-delivering (the team expects each of us to work both hard and smart); b. Over-communication (crucial for a hybrid team like us); c. do it yourself (signals how we value ownership of work and taking initiatives); and last but not least, d. don't be an asshole :)
Alex: Conno, thanks a ton!
Conno: Alex, really enjoyed this chat.
Jobs
A fresh list of startup jobs in Greece! Check it out here.
News
Endor Labs (software supply chain security) raised $93m Series B led by DFJ Growth.
Plum (fintech) secured £15m in venture debt from BBVA.
Prosperty (proptech) raised €5.5m Series A led by Eurobank.
Mood (music event discovery) announced an angel round of €1m.
Bolsterup (construction tech) raised €500k led by UniFund.
European Dynamics (IT service provider) raised funding.
Decode+ (legal AI) secured funding from Genesis Ventures.
Couch Heroes (gaming) announced a €110k round by Alter Ego Ventures.
Kos Biotechnology Partners is a new investment firm in Greece focusing on biotech and life sciences.
Greece’s national stock exchange assesses the upgrade of its electronic book building to blockchain using Sui.
Resources
Coding with AI: The end of software development as we know it with Panos Papadopoulos, Partner at Marathon, and Gerasimos Tsiamalos, co-founder of CSSIgniter.
Lessons learned from $1 billion in course sales and 23 million learners by Panos Siozos, co-founder & CEO of LearnWorlds.
To pivot or to not? by Dimitris Nikolaou, co-founder of Wondercraft.
What DoorDash got right and most others missed by Babis Makrynikolas, SVP Product & Pricing at Blueground.
An introduction to robotic surgical devices with Manios Dimitrakakis, founder & CEO of Panda Surgical.
Nuclear energy and SMRs by Georgios Laskaris, Nuclear physicist and President of Deon Policy Institute.
UX & Marketing: Balancing business goals with Michail Kouroupakis, Director of User Experience at efood.
The role of the Data Architect with Christina Kalimeri, BI & Data Analytics Manager at Cardlink.
Why centralising marketing in the AI era could backfire by Giorgos Vareloglou, founder & Managing Partner at REBORRN.
Startups don’t die. Founders quit. by Ilias Louis Hatzis, founder of Inkjin.
Events
Open Coffee Thessaloniki #87 on Apr 25
Entrepreneurship and Growth: The future perspective by NBG on Apr 28
Ctrl+Alt+Migrate: Rebooting to the cloud by AWS User Group Athens on Apr 29
Angular Athens 26th Meetup on May 6
StrictlyVC Greece on May 8
From legacy Java application to microservices by Java Athens Meetup on May 8
That’s all for this week. Tap the heart ❤️ below if you liked this piece—it helps me understand which themes you like best and what I should do more.
Thanks for reading,
Alex
Happy birthday! Thanks for the knowledge sharing and value!
Congrats! To many more. Only 95% left to 100.