A friendly investor becomes much more interesting when the next cheque is difficult to find. VentureFriends discovered that with Blueground, the furnished-apartment business it backed as a young fund. International expansion needed money. Outside fundraising did not always deliver it. The existing investor had to decide how much its confidence was worth.
For a firm whose name promises companionship, this is a useful place to begin. Venture capital has plenty of reassuring vocabulary. Founders have more practical concerns: whether someone will answer a difficult call, challenge a weak assumption or help finance a company when enthusiasm elsewhere has cooled.
VentureFriends occupies that early, awkward stretch of company-building. It invests in technology businesses around Europe and the Middle East and North Africa, usually before their futures are easy to explain in a spreadsheet. Its history offers a way to examine the work hiding behind the agreeable name.
The cheque after the pitch
In a January 2025 EUVC interview, founding partner Apostolos Apostolakis described the Blueground financing sequence. A planned 2017 raise proved difficult, so VentureFriends led the round and invested €4 million from its €20 million debut fund. In 2018, it invested €6 million from its second fund into a €12 million round.
The commitment grew during the pandemic. Apostolakis said Blueground eventually accounted for 20 percent of each of the first two funds. That is substantial exposure to one business. It also makes the story less comfortable than the usual retrospective about spotting a winner.
Of each of VentureFriends’ first two funds went into Blueground, according to Apostolakis’ 2025 account.
What initially faltered was the expectation that another investor would finance the next expansion. VentureFriends stepped in. Later came pandemic disruption and a harder financing environment. The lesson for founders is to investigate an investor’s ability to support another round before that support becomes urgent.
Apostolakis has also emphasised that Blueground’s progress depended on open communication and attention to unit economics. His public reflection warns against treating fundraising itself as success. A large round can soften scrutiny of costs just when a company needs to keep examining them.
Before the fund, an abrupt landing
Apostolakis had already experienced an operating business under pressure. In a How to Web interview, he recalled the Greek crisis forcing e-shop.gr into a fight for survival in 2011. His subsequent work included co-founding e-food and investing in other startups. Financial turbulence was part of his professional education.
George Dimopoulos joined him in angel investing. The partnership became VentureFriends in 2016. Its own five-year retrospective records a first fund of €20 million raised from 37 private limited partners and an original three-person team: Apostolos, George and Stefanos. Within a couple of years, they had invested in 20 companies.
That small beginning matters because it explains the firm’s emphasis on operating relationships. Its partners came from building and backing companies before managing a succession of funds. Experience can help an investor recognise familiar mistakes, though it can also tempt one to see a familiar pattern where a new problem deserves fresh thought.
Thirty-seven backers, then a wider map
The firm raised a €50 million second fund in 2018, with support from the European Investment Fund. Its official history places the opening of its London office that year. The third fund followed in 2021 at €100 million, alongside an expanded footprint in Warsaw and Barcelona. A fourth fund launched in 2025.
The current website reports more than €300 million under management. Those assets are capital managed for investors, not sales generated by VentureFriends. For a reader comparing financial businesses, the distinction is essential: a larger fund gives a manager more capacity to invest, but does not by itself establish investment performance.
Individual funds, not annual revenue. VF4 launched in 2025 and is excluded from this size comparison.
VentureFriends has two constituencies. Limited partners supply the investment capital; startup founders receive it and work with the team. The basic business is fund management and startup ownership, with investment returns dependent on how those holdings develop and eventually produce liquidity.
For founders, the economic exchange involves an ownership stake and a long relationship. It deserves the same scrutiny as a senior hire. A promising introduction is useful; an investor who understands why a customer will pay, or why a new market will be expensive, can be useful for years.
A grocery exit with two price tags
InstaShop gives the portfolio a different kind of evidence: a completed acquisition. Delivery Hero announced the purchase in August 2020 at a valuation of $360 million. The initial purchase price was approximately $270 million, with a deferred component for the founding team tied to subsequent growth and profitability.
The operating detail is more revealing than the headline alone. InstaShop connected customers with local vendors while shops handled logistics. At the time of the acquisition, Delivery Hero described a profitable business with around 1,500 vendors across five countries and more than 500,000 active users in the first half of 2020.
This was an investment in a service people already needed: buying groceries. Software made the connection more convenient. It illustrates why marketplace investors spend time on apparently mundane questions about fulfilment, repeat purchases and who carries operating costs. A pleasant app is only one piece of the business.
The customer’s headache is the investment thesis
VentureFriends’ explanation of its Embat investment starts inside the finance department. Cash information is scattered, payments require attention and manual reconciliation consumes time. The investors had spoken with chief financial officers before encountering the founders, giving them a problem to investigate beyond the presentation.
The distinction between customer groups mattered. Its 2024 account describes reservations about tools aimed at smaller businesses, where low contract values, churn and acquisition costs can undermine the economics. Embat’s focus on larger customers, combined with the founders’ finance experience, offered a different proposition. VentureFriends first spoke with the team in January 2022, around its first revenue.
This is a useful example for entrepreneurs preparing to pitch. The market story needs to connect the inconvenience to a buyer and a budget. A founder who can explain why a specific customer is worth serving gives an investor more to examine than a large estimate of total demand.
The same practical emphasis appears in newer sectors. In October 2025, VentureFriends explained why it had led Capalo AI’s €3.8 million seed round. The company’s software coordinates battery storage and energy trading. The investment case links renewable generation’s variability with the need to manage stored electricity more effectively.
Valeria takes the argument into payroll. VentureFriends’ March 2026 essay describes a service aimed at businesses with high staff turnover, using WhatsApp as the customer interface. Its attraction is the possibility of fitting payroll and HR support into existing working habits, particularly where another dashboard would introduce more work.
By June 2026, the investment activity included leading Kodesage’s $6.6 million seed round for legacy-software modernisation and participating in NeuralTrust’s $20 million round for AI-agent security. The connection across these businesses is an interpretation of the portfolio: VentureFriends keeps returning to costly operational problems that software might make easier to manage.
A friend who questions the assumptions
VentureFriends says it makes roughly 10 to 12 investments a year and offers help with fundraising, hiring and go-to-market decisions. It can invest before a product or revenue exists. That puts considerable weight on assessing the people and the business they intend to build.
Other seed investors offer close support too. Marathon Venture Capital, for example, also describes leading seed rounds and contributing expertise. VentureFriends’ more concrete distinction lies in its particular operating history, cross-border portfolio and examples of repeated backing. Founders should compare the partner they would actually work with, alongside the fund’s name.
“Treat intuition and investment theses as hypotheses, not prophecies.”
VentureFriends · Decision Quality in Venture Capital, 2025
Its September 2025 essay on decision quality adds a welcome complication to the language of conviction. It recommends challenging an investment hypothesis, assigning probabilities to outcomes and revisiting the original reasoning. A profitable result can flatter an unsound process; a loss can follow a sensible decision.
The exercise is easy to borrow. Write down what must be true for the business to succeed. Ask someone to make the strongest opposing case. Decide which evidence would make you revise the plan. Keep the original document so a future review cannot quietly replace earlier uncertainty with retrospective confidence.
What to ask before the first cheque
A founder considering VentureFriends can start with its published €500,000 to €3 million first-ticket range and contact form. The useful conversation then gets specific: which part of the expansion needs help, who on the team has relevant experience, and what would justify another investment?
The firm publishes a 1:2 initial-to-follow-on investment ratio. That signals the importance it places on later support; it does not make another cheque automatic. Ask how the decision will be made and how the company should plan if outside funding takes longer than expected.
The Blueground example also has limits as something to copy. Concentrating capital requires sufficient reserves and evidence that the underlying business warrants more exposure. For a founder, venture funding fits poorly when the desired business cannot support the growth and eventual liquidity its investors seek. Friendship cannot resolve a mismatch in objectives.
The revealing test comes when plans change. VentureFriends has a history founders can question in detail: who stayed involved, how much capital followed and which operating assumptions needed revision. Those are productive subjects for a first meeting. The name can supply the icebreaker.