Kikoff founder Cynthia Chen (L) and Stacker founder Noah Greenberg (R). Courtesy Kikoff and Stacker
As venture capital slows outside of A.I. and a handful of oversized deals that skew averages (like OpenAI’s latest $40 billion round), startup founders are increasingly turning to the good old art of bootstrapping—growing a company without outside capital.
“Ninety-nine percent of the founders I talk to would rather be financially independent if there’s a way of achieving that,” Cynthia Chen, co-founder and CEO of Kikoff, a credit-building fintech company founded in 2019, told Observer.
Kikoff raised about $40 million through its Series B in the company’s first 18 months. But after June 2021, Chen and her team stopped seeking outside funding. “Instead of having raised about $42 million, we could have just raised $20-something million and still be where we are,” she said. “And that would mean we would have taken less equity dilution, and the employees could have owned more of the company.”
Kikoff’s main product is a secured credit-building card. The company also provides debt negotiation, credit monitoring, rent and bill reporting services. Word of mouth has been the company’s most powerful customer acquisition channel, keeping marketing costs low. “We’d rather rely on very frugal practices and products with a really strong market fit that would bring us a lot of organic customers,” Chen said.
Some founders chose to forgo venture capital from the start. Noah Greenberg, founder and CEO of the content distribution platform Stacker, learned this lesson from his first job out of college.
“We were a venture-backed Series B company and had reached profitability. A VC board member came and spoke to the team and essentially said, ‘We didn’t give you this money to break even, but to become a billion-dollar company,’” Greenberg recalled. “Six months later, we were making decisions that were in the best interest of a venture capitalist, but not always the smartest decisions for the business.”
That experience left him wary of venture investors. “That just reiterated for me. I really want to be able to make decisions when and how I think is a best fit for the business in the long term,” he said.
Since launching in 2015, Stacker has reached $10 million in ARR. While that figure may not excite Silicon Valley VCs, Greenberg believes not every company needs to be a unicorn. “We’ve been able to take a more measured approach to when we want to take the bet that we want to take,” he said.
Yasser Elsaid launched Chatbase, a platform that helps enterprises build A.I. customer support agents, in February 2023, riding the early wave of generative A.I. “Almost immediately it went viral,” he told Observer. “Because of that traction, I never really had time to think about fundraising. I wasn’t against it, it just wasn’t my priority. All my energy went into listening to customers and shipping what they needed.”
By the time he hired his first employees, Chatbase had already surpassed $1 million in ARR, making fundraising feel unnecessary. “Bootstrapping wasn’t a deliberate ‘anti-VC’ stance at the start,” he said. “It was simply a byproduct of focusing 100 percent on customers. But as we grew, it became clear that staying lean and independent was a strength.”
None of these founders dismisses venture capital outright. VC money can provide breathing room that bootstrapped companies don’t always enjoy, and in some cases, it’s essential to getting off the ground. But they agree that the system’s incentives often clash with the realities of building a sustainable business.
VC firms invest in high-growth, early-stage startups with the expectation of outsized returns. But the risk is high. On average, only one in 10 VC-backed startups eventually delivers expected returns. “VCs are looking for 10x exits because their wins need to make up for the other nine losses,” said Greenberg.
In today’s tech world, funding announcements are so celebrated that companies without them can struggle to hire or establish credibility. Yet the market often forgets that many of the industry’s most successful players—Microsoft, eBay and Dell among them—largely bootstrapped their early operations without outside capital. Now, with A.I. making it easier than ever to launch a company and build a product, venture funding isn’t as essential as it once was.
Kikoff had 17 employees at the time of its last funding round in 2021. Despite a lack of follow-up fundraising, the company has grown into a team of more than 130 people today and generates hundreds of millions in annual recurring revenue (ARR). It became profitable in 2023. Chen, who managed Kikoff’s payroll herself for a while to conserve funds, is preparing for a move to a larger office next month.
Greenberg, who wanted to avoid giving a board voting power—a common condition of VC funding—still sought expert guidance. To strike a balance, he set aside 2 percent of equity for an advisory board, gaining support without ceding control. Elsaid, meanwhile, tackled the challenge of lacking the credibility that big funding rounds often bring by creating his own proof: publicly sharing milestones, partnerships and other wins. In just two and a half years, Chatbase has grown to $7 million in ARR.
Elsaid believes the cultural shift is already happening. “The next generation of founders are much less likely to default to pitching VCs before even building a (product),” he said. “They’re more willing to question whether they actually need it.”
