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.
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.
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).
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?
Table of contents
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
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.
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.”
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.
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.
Both are legitimate. But they are not the same game. And you cannot play both at once.
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.
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.
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.
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.
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.
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.
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.
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.”
So before you take the plunge, flip the thought process. Convince yourself that you should raise a venture round; ask whether you should take that big round. Ask yourself why this opportunity uniquely demands it — whether the market dynamics, the competition, the capital intensity, or the speed required make it genuinely impossible to win any other way.
And then, once you’ve wrestled with that yourself, talk to the people who matter most. Your co-founder. Your spouse or partner. Your advisors. Not to brief them on a decision you’ve already made, but to think it through together.
Two things need to happen in those conversations:
First, they need to understand what you are actually signing up for. Because when you take venture capital, they are signing up for it too. The late nights, the uncertainty, the moments of acute stress where you might be at your worst, the years of deferred everything. And the very low, single-digit percentage chance that you are successful in a meaningful financial way. That should not be an easy decision, and you need your core partners there with you 1000%.
Second, use them as a sounding board. Let them pressure-test your reasoning. Make sure the answer to “why raise venture?” is a good enough reason. Convince them.
If your answer is to go all in and raise venture capital, here is what you are committing to.
This does not mean overtly lying. Unlike Box slapping “AI” on a billboard for a product nobody uses for AI (and almost certainly never will), you do not need to fabricate reality.
But like the other tech companies with billboards on the 101, you do need to loudly communicate a bold vision worth billions. And, as Nikhil Trivedi, Co-Founder and GP at Footwork, said, your ambition cannot be “delusional. [The best pitches are] grounded in something you’re already seeing show up in the product or the business. A real unfair advantage…there’s a foundation for why it will actually happen.”
Ideally, your vision is consistent with the tech zeitgeist (today, AI); it is far harder to raise, recruit, and win when you are an antipattern.
More importantly, being venture-backed means you need to get good at “faking it” and selling that vision with conviction. Properly doing so requires that you ground your vision in reality (unlike Box), and sell to the market where you are going (not merely where you are). This matters to every stakeholder, not just your investors.
Your customers, especially your earliest ones, are buying into a promise about the future. Your employees are investing their most precious resource (their time) in making your vision real. Their time better be worth it.
Your ability to sell the vision is what creates the conditions for the reality you are describing. Not the other way around.
You probably think your idea is unique. It isn’t.
Any genuinely venture-scale idea has almost certainly already been thought of by someone else. If you don’t have direct competitors today, you will soon. And honestly? You should want them. Good competition is validation that you are onto something real; competition helps teach your market, so you don’t have to do all the work.
If you can’t find competitors, that usually means one of two things: you are lying to yourself, and your competitors are obvious to everyone else, or the opportunity isn’t as good as you think.
Your job is not to find a blue ocean. It is to find the biggest possible market you can compete in. And then, as Kyle Porter, Founder and CEO of Salesloft, did, “out innovate, out execute and outlast” the other sharks in the water.
Profitability still matters. If you are venture-backed and you can be profitable, you should be. But it does not define success in this game. Your investors don’t want dividends. They want massive outcomes that return the fund.
As Ian Sigelow, Co-Founder & Managing Partner of Greycroft, shares, “there are only 20 companies that go public every year.” These are the companies they look for, the ones that “can go from zero to a billion in revenue.” Your goal is to become one of them.
For most businesses, 25–30% annual growth is exceptional. For you, it is a disappointment. Your investors will always ask why things aren’t faster. Your employees will consider leaving for a company that is growing more quickly. At the growth stage, VCs want to see a growth rate of at least 100%, and ideally, it’s much higher.
The exact profile of your team will vary depending on your business, market, and stage. But B and C players will not cut it. You need to believe with conviction that the people surrounding you are the best possible fit for your company, whether they are your co-founders, your first hires, your engineers, or your leadership team.
These are the people who will drive your slope, who will out-innovate your competitors, and who will stay when things get hard — because they believe in what you’re building. As Rob LoCascio, Founder and former CEO of LivePerson, believes: A players are those with both “skill and will.”
The impact gap between a B and an A is enormous. It is easily ten times. In today’s world, where A are now building agents that serve as personal force multipliers, it is likely much higher. When you know someone isn’t right, move fast. Every week you wait is a week your competitor isn’t waiting. The opportunity cost of the wrong person in the seat (especially when you’re early stage) is huge.
When I was pushing through one of the hardest stretches at Workstream, my friend Bart Hacking, BetterCloud’s former CFO, said something to me that I often think about when coaching CEOs: “Keep going. You knew this was going to be hard. If it were easy, anyone would do it.”
He was right, but here is what I would add: the steeper the hill, the more ambitious the goal, the more competitive the market, the higher the valuation, the bigger and more capable the team — the harder all of it becomes for you. The stress compounds. The personal sacrifices multiply. The things and relationships that matter outside of work are harder to maintain.
You have to be brutally honest with yourself about how you’re managing, what you need, and how you’re caring for yourself. That’s the foundation for caring for the business. As Itamar Zur, Co-Founder and CEO of Veho, instructs: “Take really, really, really good care of your body and your mental health. Make it the number one priority. Everything stems from that. If you don’t have that, you are not going to make it.”
The more you acknowledge to yourself (and those you trust) how hard it is, the more you can ask for help. And in a game where you will be stretched incredibly thin, and the stakes are incredibly high, every little bit of support materially impacts how well positioned, or not, you are to win long term.
The Grail Knight doesn’t stop you from choosing the wrong cup. He just watches. And when you choose poorly, the consequence plays out exactly as it has to.
Don’t let that be you.
Be intentional. Don’t let hype, FOMO, or outside pressure push you onto a path that is wrong for your business and for how you actually operate. The billboards on the 101 will always be loud. The buzz will always make the all-in, venture scale path feel like the obvious choice. It isn’t.
And know this: once you cross that threshold, you cannot uncross it. The decision to go big can appear as early as day zero, when all you have is a pitch deck, an idea, and a customer you want to build for. Most founders don’t even realize they’re looking at it. They sign the term sheet, the money hits the account, and the choice has been made — whether they were ready or not.
Choosing wisely doesn’t mean choosing a safe path; either path can kill you. Risking failure is the deal we all make when we choose entrepreneurship. But there is almost certainly one path that is most right for you: for your personality, your business, your market, and the people depending on you.
Once you have taken VC, the decision has been made. Be intentional with your decision.