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Key Takeaways
- Startup advice is built on someone else’s context. Rules like “raise as much as you can” or “move fast and break things” worked in specific situations and may not fit yours.
- Question advice before you follow it. Ask why it exists and whether those conditions apply to your business, and seek out people who have faced situations like yours.
Every founder gets advice, and most of it comes with conviction. Find a clear market gap. Raise as much as you can. Get a technical co-founder. Much of it is useful, but very little of it comes with the context that made it true in the first place.
I learned this firsthand while building a company in real estate technology. When we were raising our Series A, an investor told us the market was too competitive and already had too many players. Standard advice for early-stage startups is to find an open lane before going in. That advice made sense in the situations the investor had seen succeed. It didn’t make sense for ours.
Real estate tech was crowded, but it was crowded with mediocre software. There was no clear winner, which meant there was still room to win.
We focused on a segment most people had written off as too small, the top 1% of agents, and built premium software and service for them first. We bootstrapped to $1 million in revenue before raising anything. By the time we took investor money, we understood our customers well enough to know which conventional wisdom applied to us and which didn’t.
That distinction, between advice that’s generally true and advice that’s true for your situation, is something I come back to whenever I talk with founders, whatever their industry.
Why startup advice turns into rules
Most startup advice comes from pattern matching. Someone succeeded doing X, so X becomes gospel. The advice travels faster than the context behind it. The problem isn’t that the advice is wrong; it’s that it stops being advice and becomes instruction.
Wisdom specific to one situation gets turned into a rule everyone follows, whether it fits or not. We chose our own route, knowing we didn’t fit the pattern the advice was designed for. Here are five startup “rules” we broke.
1. Raise at the highest valuation you can get
The conventional wisdom is to take the best terms available. There’s logic to that, but raising at 200 times revenue means spending years trying to grow into numbers that were never grounded in your actual business.
We raised at valuations that let us keep the right partners, limit dilution and run a company that worked. Some companies in our market raised too much at valuations that were too high, and they’re now stuck because their last round set a bar that may take a decade to clear. We didn’t want that to be us.
2. Raise as much as you can
This is a related trap. The argument is that more capital means more runway and more options. In many cases, it actually produces waste and a company that never has to make the hard choices that force you to understand what matters. We raised what we needed to reach the next milestone, plus a buffer, and that discipline paid off.
3. You need a technical co-founder
I’m a solo founder who hired great engineers instead. For a long time, investors flagged that as a structural weakness. I don’t think it is, and with what AI makes possible now, the argument has only gotten weaker. You do need strong technical talent, but you can hire for it.
4. Move fast and break things
This piece of startup doctrine has aged poorly faster than almost any other. With AI coding tools, anyone can ship software quickly, so the supply of mediocre products is now essentially unlimited. The only way to win is to build things that are actually great: well-designed, well-tested and genuinely useful.
That’s especially true in high-trust industries. In real estate, customers are making the largest financial decisions of their lives, so the tolerance for broken things was never high. Trust takes years to build and can be lost quickly. Moving carefully where it matters isn’t a concession. It’s a product strategy.
5. Disrupt from the low end
The classic playbook says to enter at the bottom of the market, undercut on price and work your way up. We started at the top and built from there. Those early customers gave us deep product knowledge, a strong reputation and references that eventually carried us further into the market than a low-end entry would have.
None of this was the “right” approach according to startup playbooks. It worked because we understood our customers and market well enough to know where the standard rules applied and where they didn’t.
The better question to ask
When you’re early in building a company, you’re surrounded by people with strong opinions about what you should do: investors, advisors and other founders. Much of that advice is offered in good faith. But a lot of it is based on situations that look similar to yours on the surface and are actually quite different. Listening is smart. Accepting it without question, as if context didn’t matter, is the mistake.
A better habit is to treat advice as a prompt for questions rather than a directive. Why does this advice exist? What conditions made it true? Do those conditions apply to my business, my market and my customers? Sometimes they will, and sometimes they won’t. The answer is almost always more valuable than the advice itself.
My recommendation: Find people who have done the specific thing you’re trying to do, in conditions that resemble yours. Ask them why they made their choices, not just what those choices were. The context is the useful part. Without it, you’re following someone else’s map through terrain that may look nothing like theirs.
Key Takeaways
- Startup advice is built on someone else’s context. Rules like “raise as much as you can” or “move fast and break things” worked in specific situations and may not fit yours.
- Question advice before you follow it. Ask why it exists and whether those conditions apply to your business, and seek out people who have faced situations like yours.
Every founder gets advice, and most of it comes with conviction. Find a clear market gap. Raise as much as you can. Get a technical co-founder. Much of it is useful, but very little of it comes with the context that made it true in the first place.
I learned this firsthand while building a company in real estate technology. When we were raising our Series A, an investor told us the market was too competitive and already had too many players. Standard advice for early-stage startups is to find an open lane before going in. That advice made sense in the situations the investor had seen succeed. It didn’t make sense for ours.
Real estate tech was crowded, but it was crowded with mediocre software. There was no clear winner, which meant there was still room to win.
