Dispatch issue #5 - Startups
A favorite myth in startup culture is that the most valuable companies are built fast, scaled instantly, and led by visionaries who live to break rules and move on before the dust settles.
Although a compelling story, one not devoid of truth, a closer look reveals that most successful startups (the ones that last) are actually built methodically…slowly, even.
They obsess over things that don’t scale.
They spend days writing six-page memos.
They say no to easy growth.
They onboard customers carefully.
In other words, successful startups are often contradictions. They move fast, but only after moving slowly. They obsess over efficiency, but do things the hard way first. They’re built for scale, but with the care of a craftsperson.
In a climate where capital is tight, attention spans short, and trust is harder to earn than ever before, this contradiction isn’t a liability.
It’s leverage startups use to maximize their potential.
MOVE SLOW AND KEEP THINGS TOGETHER
There’s a reason why one of Paul Graham’s most popular essays is titled, “Do Things That Don’t Scale.” It’s not because growth is unimportant. It’s because depth precedes scale. And depth takes time.
Main Street Summit Startup/Venture Track speaker Victor Zhang wishes he ignored advice from startup gurus early in his business building journey. Now the Co-Founder and CEO of Trestle, the gurus told Victor he needed to figure out how to build a company that could scale. In fact, the opposite is true.
In Victor’s own words: “Startups live in 12-24 month cycles and don’t have the luxury in the early days of building like it’s going to be a lasting company.”
By definition, companies that last have achieved scale. But achieving scale early doesn’t necessarily mean a business will last.
Consider how Jeff Bezos banned PowerPoint in favor of six-page narrative memos. He believed clear thinking demanded exhaustive writing, and writing, unlike short and punchy PowerPoint decks, demanded clarity.
Casey Williams, Partner at early-stage investment firm Fenway Summer and Main Street Summit Startup/Venture Track speaker, says writing is one of the most significant tactical decisions she’s made that’s changed how she operates her firm.
“Recently we’ve implemented a writing-heavy approach to our investment process centered around memos that expand in length and complexity as we move from initial to detailed diligence, similar to the decision-making culture Jeff Bezos describes at Amazon.
The way writing clarifies my thought process, better prepares our team for meaningful conversations, and uncovers potential blind spots or areas for follow up has made our process significantly more effective, but it’s also actually made it more efficient as well.
At first it felt cumbersome to write reports where a live conversation would have normally been sufficient, but it turns out the ability to work async by sharing information through writing cut down on meeting times, and those meetings were more productive because everyone was coming to the table with the information they needed, so we didn’t have to spend the first 20 minutes getting everyone up to speed.”
Here are a few other popular examples: Airbnb founders manually photographed their first listings. Stripe’s founders flew city to city to install code for early users. At Ramp, Eric Glyman (Main Street Summit 2025 speaker) and his co-founders ran the entire customer onboarding process themselves, end-to-end, long after they had traction.
From the outside, it all looked fast. But inside? It was a thousand tiny, deliberate decisions and actions.
This is the part most people miss. And it’s the part that’s most instructive to those starting or building companies of any size today.
SPEED GETS HEADLINES. SLOW & STEADY BUILDS COMPANIES.
Five years ago, speed was status. Today, durability is.
Here’s some of what we’re seeing and hearing:
Venture funds shifting attention from blitzscaling to profitable business models.
Startups celebrating sustainable revenue and high-margin products and services.
A return to “boring businesses” that grow reliably and quietly.
Slowness used to be a liability. Today, it signals focus, clarity, and the discipline to say no.
THE TAKEAWAY
You don’t need to raise $10 million to operate like a great startup. Nor do you need to grow 10x overnight to benefit from the so-called startup contradiction.
Here are a few actions to implement in your own business:
1. Do Things That Don’t Scale On Purpose
Don’t outsource trust. Deliver early customer experiences manually, directly, and with obsessive attention. You’ll learn faster and build real loyalty.
2. Make Thinking Visible
Replace long meetings with short writing. A memo beats a brainstorm every time. Remember that clarity scales while confusion multiplies.
3. Revisit Your Convictions Slowly
Fast growth is exciting, but long-term resilience requires deep belief. What do you know about your customers that others overlook? Sit with that question. Then act based on what you discover.
4. Design Your Own Slowness
Make slowness a feature of your systems, not a bug. For key decisions like hiring and strategic initiatives, build in time for thought, feedback, and silence. Sometimes a two-day delay is worth two years of alignment.
THE REAL STARTUP PARADOX
In 2011, Marc Andreessen wrote that “software is eating the world.” And it did. But the startups that survived the feeding frenzy weren’t just the fastest or loudest.
They were the ones that paired ambition with patience. That’s the contradiction at the heart of great companies.
The best part? You don’t need to be a startup to build that way. You just need the courage to be deliberate.
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