What venture capital demands from founders and CEOs

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Lessons Earned<br>Fake it, or don’t. There is no middle way<br>What being venture-backed demands of you

Nicholas Freund<br>May 21, 2026

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I was recently in the Bay Area, driving up Highway 101 to San Francisco for breakfast. On this particular drive, I could not help but notice the latest billboards. If you have never been to the Bay, the billboards in this tech mecca are uniquely revealing: they offer a real-time snapshot into who is “crushing it” in the industry, what’s trending in tech, and where things are going.<br>Today, every single billboard is about AI. AI infrastructure, AI agents, AI transcription, AI-everything. Not a single one that doesn’t reference AI in some capacity.<br>As someone immersed in tech and an early adopter of AI tools, I expected to recognize most of these companies. I knew and used some of these tools, like Claude and Granola, but most of the billboards were for companies I’d never heard of.

And then there was Box. A company that’s been around since 2005, loudly positioning itself as an AI company. Despite the reality we all know: no one actually uses Box for AI (or likely ever will).<br>Then I started wondering, are any of these claims actually real? Or are founders just faking it? Is faking it necessary to succeed in tech today?

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Table of contents<br>Go all-in, or don’t

Be intentional about how you fund the business

Your vision needs to be massive

Embrace the competition

You need steep growth

You need a team of A players

The personal toll will be massive

Go all-in, or don’t

When I arrived at breakfast, I asked my friend J Zac Stein, the Co-Founder and CEO of Span, how much he thought founders have to fake it.<br>His immediate response, with a smile on his face: “The reality is, unlike what Buddhism teaches us, there is no middle way. You either have to be fully bought in or not play the game at all.”<br>J Zac (ironically, a practicing Buddhist) is right. And I don’t think most founders fully internalize what “all in” actually means until it’s too late.<br>Here’s the simplest way I know to say it: when you set out to build a company, you’re making a binary choice. You are either swinging for the fences — building something designed to return a venture fund, to hit $100M ARR, to be worth a billion dollars (and today, that isn’t even enough) — or you’re building something else.<br>Both are legitimate. But they are not the same game. And you cannot play both at once.<br>To paraphrase the Grail Knight from Indiana Jones and the Last Crusade: your path is yours to choose when you set out to build. But choose wisely.<br>Because here is what most founders don’t realize until they’re deep in it: the choice often gets made for you, earlier than you think.<br>The moment venture capital hits your bank account — real venture capital, from a real fund, at a real valuation — you’ve crossed a threshold. Whether you felt it or not, whether you were fully conscious of it or not, a decision has been made. You are swinging for the fences now. The investors who just wired you that money did not do so because they believe in a nice, sustainable, cash-flow-generating business. They believe you can return their fund many times over.<br>And once that money is in, there is no middle ground. You can’t half-commit to a $500 million outcome. You can’t hedge your way to a venture-scale return. You go all in, or you spend the next several years slowly disappointing everyone: your investors, your team, and eventually yourself.<br>Be intentional about how you fund the business

When I set out to build Workstream, raising VC money felt like the only choice. At the time, I didn’t clearly see any other way to build the company.<br>I don’t regret the decision, but I do wish I had been more honest with myself about what it actually meant before I signed that first term sheet: years of trying to become the next “it” company; competing for buyer attention in a crowded market; the exhaustion of constantly being on the financing hamster wheel; the enormous growth pressures; the exhaustion of recruiting and retaining the best possible employees; the late nights and personal toll. The stress that comes with being responsible for the livelihood of dozens of people, and knowing that millions of dollars were on the line.<br>Share<br>And I do wish someone had reminded me that taking VC money is actually a choice. Most business owners never do it. They build something real, something profitable, something they own — without ever taking a dollar from a fund.<br>For most of us living in the tech bubble, we forget that bootstrapping is not the fallback option. Bootstrapping is the default option. Venture capital is the exception, and we should treat it that way. As Flint Lane, Founder and CEO of Billtrust, shared, “Don’t forget that there are no prizes for raising a hundred million in your first six months. There are prizes for building a great business.”<br>So before you take the plunge,...