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How to Build a Startup in the Sequoia Way: The Story of Calliper

Image credit: James Elmore (left) and Kosta Kolev (right), co-founders of Calliper
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Kosta Kolev had his first encounter with tech while working in a computer repair store in his hometown Plovdiv in Bulgaria. Ever since he was instilled with inspiration to solve technology problems. 

Kosta Kolev is a 28-year-old Bulgaria-born entrepreneur who emigrated to the UK together with his family around 20 years ago. He is the co-founder of Calliper, a startup that aims to help other startups take control of their operational data and break down silos between different teams. Kolev is one of the founders who got into the inaugural cohort of the Sequoia Arc accelerator programme for European seed companies. 

In June, Calliper closed a $1.8M seed round from Sequoia, Moonfire Ventures, LAUNCHub Ventures, Verissimo Ventures, Tiny.VC and a group of angel investors.

“I have always been fascinated by technology even while I was just playing a computer game. But the engineer in me always wanted to know how it all comes together. I spent my teenage years teaching myself how to use Photoshop and various design programs. Then things really took off for me when I got to university. As someone who was still not 100% confident in their English, I focused my attention on digital publishing and digital products. Learning how to build digital products means that you can get so much more exposure and literally reach anyone in the world. It was this potential of scale that captured my imagination,” Kolev shares for The Recursive. 

The Recursive met with Kolev to learn more about the story of the young Bulgarian diaspora founder and his insight into what it takes to get into the accelerator of the legendary Sequoia. 

Learning entrepreneurship on the go

Kolev categorizes himself as being quite lucky for going through the typical mistakes of first-time founders in his early 20s. “What I mean is working with people who are brave, but don’t have the right kind of values, building products that you are personally excited about without a specific market need, or spending too much time on strategy and not enough time on implementation,” he explains. 

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From a lifestyle app for nutrition and food waste reduction to a smart home thermostat solution, and a boutique innovation consultancy company, Kolev has been through it all. He says that failure taught him a healthy appreciation for the founder’s journey and made him think in a more mature and composed way. 

According to Kolev, one of the most interesting things that founders must reflect on is whether they can authentically speak to the product that they are building and to the market that they are servicing. Or put in other words, their founder-product-market fit. 

“As Calliper started to take shape, together with my co-founder James Elmore, I became passionate about helping other founders think systematically, measure and monitor different metrics across the organization more effectively, and collaborate with data across the organization to break down silos between different teams,” he explains. 

Calliper is a collaborative analytics platform that integrates via APIs all the standard operational tools that are used to run any business. These include Stripe for payments, Xero for accounting, HubSpot for sales teams, and Google Analytics for monitoring of marketing campaigns. Calliper integrates into all of these different tools to develop an aggregated view of how the business is performing and to create a common interface where everyone in the company can see insights and alerts. 

The company services early-stage startups with around 10 to 30 employees, who are starting to feel some of the pains around growth. The fact that Kolev has spent the last 10 years of his life working with early-stage founders and launching his own ventures, tips the scale to his advantage. At the moment, they are co-creating with a handful of early-stage founders. 

Building a startup the “Sequoia way”

During their fundraising process, the co-founders of Calliper spoke to almost 120 investors. Their main goal was to opt for the people who not only had experience but a growth vision. “We wanted to get on board those investors and partners who were thinking how the company will look like in 5 or 10 years from now,” Kolev shares.

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Having won itself a reputation as a legendary VC that takes founders from idea state to an IPO, Sequoia was a natural destination for the founders of Calliper. 

Around 3000 seed companies were competing to secure spots in the first cohort of the VC’s accelerator program. Calliper was among the 17 winners who received $1M financing and access to the 8-week mentorship program for building a company in the “Sequoia way”. 

“Everything just felt very collaborative, in terms of how we came together, how we saw the business, and how we saw the market. Of course, the pressure and the high intensity during the pitch are undeniable. But all the interaction that we have proved that Sequoia cut above the rest in their focus to be a long-term partner,” Kolev highlights. 

Right now, Calliper is in the homestretch. The team has around one more week of doing remote work after which in mid-July they will be heading to San Francisco, where the program is going to finish. 

Learning and teaching entrepreneurship

“Entrepreneurship is like an apprenticeship. You learn from the best and then pay it forward. And this is something that I am trying to do more and more of, especially in terms of connecting back with the Bulgarian ecosystem,” says Kolev. 

As a person who wants to stay connected with early-stage companies and give back to the startup ecosystem, Kolev spends a lot of time mentoring and going to various events where he connects with young founders. 

Even to this day, he remembers Rick Lomas, a guy that he worked with in a small dev shop and the first person who was incredibly influential to him in his career. “The whole process of learning from people who are either at the same stage as you are a little bit further ahead is the best thing you can do as a founder. This tribal mentality is something unique and special with the startup community and I hope it never fades as companies start to grow,” he outlines. 

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On a journey to create product love

“In the field of collaborative analytics, Calliper is developing a product that serves even the youngest companies with the smallest of teams; it helps them make sense of heaps of data from fragmented sources without the privilege of having data scientists on a payroll. That’s why we see Calliper not only as an exciting investment – their product potentially accelerates the development of other software startups as well. Kosta’s venture positively changes the way other startups operate, palpably contributes to their success, and boosts the development of the ecosystem. What’s not to love? We’re confident Kosta and James are going places with their approach,” Stephane Gantchev, Partner at LAUNCHub Ventures comments on the latest investment. 

For the next 12 to 18 months, the team of Calliper will stay focused on finding the magic formula of product-market fit and healthy growth. After graduating from the program, Calliper will be looking to raise the following round and prepare for bolder scaling.

“Right now, we want to keep the team and the customer engagement as small as we possibly can until we are fully confident that we have found a formula that works. We are also considering Bulgaria as a potential place to open our engineering hub once we are at that stage. Until this happens, we will be searching for local product engineering talents with whom we can achieve a good company culture fit,” Kolev concludes. 


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Elena is an Innovation Reporter at The Recursive, an online media dedicated to the emerging tech and startup ecosystems in Southeast Europe. She is keen on sharing the innovation stories that shape the regional ecosystem and has a great interest in fintech, IoT, and biotech startups. Elena is currently finishing her Bachelor's Degree in Business Administration and Political Science at the American University in Bulgaria.