Matthew Prince on Co-Founders, Ambition and Cloudflare’s Early Growth

Matthew Prince grew up with parents who started bootstrapped businesses and experienced both success and failure. He assumed that starting a company was simply what adults did. His first remembered sale was illegal fireworks to schoolmates, a business that made him popular with children but not their parents.

Before Cloudflare, Prince had an anti-spam business, Unspam, that he says was not especially successful. Its engineers built side projects, including Project Honey Pot, which gathered information about how spammers harvested addresses. He says about 100,000 people eventually signed up and many asked whether the system could stop attackers as well as observe them.

Prince initially dismissed that request because implementing it seemed difficult and large. At business school he met Michelle Zatlyn, who recognised the opportunity in Project Honey Pot. Prince credits her, rather than himself, with the key realisation that they should build a company around stopping threats.

He says founders need either to love their work or grow to love it because a successful company can occupy many years. Defending the internet was not originally his central passion, but he says he became more attached to Cloudflare’s mission over time. He has a direct interest in the company as co-founder and CEO.

On Cloudflare’s thirteenth anniversary, Prince contemplated whether he should still lead it thirteen years later. He believes founders can stay too long and prevent successors from contributing, but also worries that some successful founders struggle with identity after leaving. His comments about individual founders’ happiness are personal impressions, not evidence about their private lives.

Cloudflare reflects more than one founder, Prince says. He credits Zatlyn’s different strengths with shaping the company alongside his own, and says their ability to have difficult conversations without sustained conflict sets a tone for the organisation. Picking complementary co-founders, in his view, is one of an entrepreneur’s most important decisions.

Stebbings asks whether happiness must be traded for success. Prince says impact is part of what makes him happy. He recounts Cloudflare’s support for Ukrainian government and infrastructure organisations around Russia’s 2022 invasion and says the company offered services without charge; he also describes being sanctioned by Russia. These are his accounts of Cloudflare’s role and motivations.

Prince also says people organising protests in Iran have used Cloudflare technology for privacy and security. He values the ability to make such a contribution while remaining relatively anonymous. When Stebbings asks about a rumour that he offered to resign after a security incident, Prince explicitly says it never happened.

Prince contrasts Cloudflare with Unspam, whose co-founders were childhood friends with very similar skills and backgrounds. He says overlapping roles led to fights over who was in charge and damaged friendships. For Cloudflare, he deliberately sought people whose abilities complemented his rather than simply selecting close friends.

In Cloudflare’s early days, Prince says he handled sales, marketing, product and support; Lee Holloway concentrated on engineering; and Zatlyn built operational processes, including recruiting at scale. He likens a founding team to overlapping circles that should cover as much of the problem as possible while retaining enough common ground to work together.

Prince and Zatlyn were not close friends when they started, but became close through years of working together. He sees professional respect and complementary skills as a stronger starting point than friendship alone. He also acknowledges that other arrangements can work, even though he considers being married to a co-founder particularly difficult.

Clear decision rights help the pair disagree and commit. Prince says he ultimately decides product questions, while Zatlyn has the final call on areas including sales, marketing, support and HR. He recalls her confronting him for behaving disrespectfully in a meeting; he apologised and says he worked to change his behaviour.

Prince argues that diverse teams can see different problems and perspectives and attributes part of Cloudflare’s development to the differences among its founders. His experience is an argument for complementary viewpoints, not proof that every diverse team will outperform. He then acknowledges that his focus on work damaged some personal relationships.

He says he was deeply in debt when Cloudflare started and had borrowed money from his mother. The November 2009 funding round arrived close to his rent deadline, and payroll depended on closing it. Later financial stability, he says, helped him feel ready to prioritise marriage alongside the company.

The central disagreement began with Stebbings’ advice to venture-backed startups: target an extremely narrow customer segment before product-market fit, then earn the right to expand. Prince strongly disagrees with that formulation. Both agree their debate concerns the venture-funded path, not every kind of business.

Prince says a niche can make sense for a bootstrapped company, but venture capital has a different set of expectations. He sees three broad outcomes: exceptional success, quick failure and a long slog that grows just enough to keep going without achieving the desired result. He considers the last especially costly in time and motivation.

Because quick failure is possible, Prince says Cloudflare did not raise friends-and-family or angel money before its IPO. His concern was losing money from people who could not afford the risk; professional investors understand that startups can fail. This is his account of the company’s financing choice, not a guarantee of any investment outcome.

Prince argues that recruiting talented people requires an ambitious vision. His hypothetical contrasts software for a small group of snowboard shops with a platform that gives merchants an alternative to Amazon. Stebbings replies that a compelling vision can coexist with a specific starting point and a credible journey to the larger opportunity.

Prince recalls saying at an early TechCrunch pitch that Cloudflare’s vision was to run the internet. He believes that ambition attracted people who might not have joined a narrowly framed security product for small businesses. Stebbings maintains that starting with one customer group does not require abandoning the bigger ambition.

Cloudflare faced a chicken-and-egg problem: it needed customers and data to develop security models that could serve large organisations. The company launched a free service broadly, expecting startups and individual developers to sign up. Prince says the actual mix differed from that expectation.

Civil society and human-rights organisations, he says, had little budget but faced substantial security risks and adopted the free service. He believes a narrowly defined initial target could have caused Cloudflare to miss them. This is a company-specific retrospective, not proof that all startups should use the same approach.

Stebbings responds that Prince’s example is specific to Cloudflare and that a targeted ideal customer profile can help win the first true fans. Prince says he supports learning deeply from early users after casting a wide net, but worries that choosing too narrow a market in advance can miss unexpected demand or lead a team to optimise for a small end state.

Stebbings continues to distinguish a broad vision from a focused initial customer, noting that messaging and sales must resonate with buyers today. Prince agrees that concrete execution and early customers matter, but argues founders should communicate the larger ambition to recruits and investors. Their disagreement is over how narrowly to constrain the initial target, not whether to learn from customers.

Prince names poor co-founder selection and insufficient ambition as two major founder mistakes. Stebbings adds choosing a bad market; Prince agrees that a market too small to support an important outcome is a problem. Both are offering judgments from their respective experiences, not a complete ranking of all startup risks.

Cloudflare’s founders were outside the most connected startup circles, Prince says, which helped them concentrate on building. He emphasises that a successful business need not be venture-backed or public. He describes entrepreneurs building bootstrapped software companies for cash flow, though Stebbings wonders whether concentrating on one could produce a larger result.

Prince cites Tough Mudder as another example of a business that may offer meaningful success and flexibility even if its public profile or paper valuation differs from Cloudflare’s. This is his comparison and characterisation, not a verified accounting of the other company’s economics.

Not having enough money to pay rent was distressing, Prince says, but after basic security and family needs are covered, additional wealth has diminishing personal value to him. He measures success partly by whether Cloudflare improves the world and creates opportunities for its employees, including an employee who told him they could buy a dream home.

Prince says everyone who invested before Cloudflare’s IPO made at least ten times their investment. The interview does not specify the measurement date, whether those gains were realised or how each investor’s return was calculated. He says venture investors can add value but urges founders to choose the individual partners carefully.

He compares venture partnerships to relationships that are hard for either party to exit, which can make candid conversations difficult. Public-market investors can sell if they disagree, he argues, and may still take a long-term view. He cites Baillie Gifford’s claimed average holding period of 16 years as an example, without giving a source or measurement period.

Asked about his biggest regret, Prince recounts Cloudflare co-founder Lee Holloway’s behavioural changes and departure. Prince says he initially interpreted them as a change in character, then learned Holloway had frontotemporal dementia. He regrets his anger and the way the situation was handled; this is a personal account, not a general way to diagnose changes in behaviour.

The experience led Prince to ask whether a dramatic behavioural change might reflect personal circumstances or health. He also values colleagues who challenge his strongly held views. A CEO’s statements can be treated as correct merely because of their source, making independent questioning especially important.

Prince says he admires Tim Cook’s principles, including his views on privacy, and would also like to talk to historical thinkers about rule of law. He connects both interests to trust: large companies and governments must find ways to demonstrate that people can rely on them.

Asked what would take Cloudflare from roughly $20 billion in market capitalisation to $200 billion, Prince recalls his calculations of shareholder value created per day at Cloudflare and Salesforce over selected ten-year periods. Those are his retrospective estimates of changes in market value, not cash realised by investors.

Prince believes subscription businesses can compound and says Cloudflare is on a path from $1 billion to $5 billion in revenue. He describes reaching that figure as inevitable, but it is his forecast, not an established result. He expects the company and others to become much larger; the future valuation is speculative and he has a direct interest in Cloudflare’s performance.