March 24, 2025

The Progress Report

Being an entrepreneur rocks, in a lot of ways. But it can also be pretty freaking frustrating. Such as when you’re sitting there, completely stuck on a problem, and don't feel like you have anyone to call.

That isolation isn't just the emotional burden of entrepreneurship, though. It's a strategic disadvantage. 

The most successful founders aren't lone wolves. They're deeply connected to communities that challenge their thinking, validate their approaches and keep them sane when things get rough.

In this newsletter:

• How Figma turned vulnerability into community, and community into product

• Networking that focuses on connection, rather than business cards

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Weekly Insight

When Dylan Field and Evan Wallace started Figma, the challenge was pretty daunting, right out of the gate. They were trying to enter a market dominated by Adobe, a $300+ billion giant with decades of customer loyalty.

Conventional startup advice would have them perfect their product in secret, but they weren’t having it. Instead, Figma chose vulnerability as a strategy.

For over two years during development, they regularly invited designers to see their unfinished work. No polished demos, just honest conversations: “Here's what we're building. What do you think?”

When designers saw their feedback implemented in later versions, something powerful happened. They transformed from testers into collaborators, and felt genuinely invested in Figma's success.

Turns out, people respect vulnerability—especially when you pair it with an earnest attempt to improve.

This approach created relationships that money couldn't buy. By launch day, Figma had influential advocates already championing their product across design teams and companies.

The results were remarkable. Figma grew rapidly in a crowded market, eventually commanding a $20 billion(!) acquisition price in 2022. But their true achievement was building a community so loyal that even Adobe's purchase couldn't diminish their enthusiasm.

The lesson? Real connection outperforms perfection every time. By being open about their work-in-progress—and taming their egos enough to accept feedback!—Figma created a competitive advantage no marketing budget could match.

Intent to Action

Bad news first: real connection can't be manufactured through formulas or platforms. It requires authenticity and a willingness to contribute without immediate expectations of a return. AKA the long game.

Now the good news: playing the long game doesn’t take as long as you’d think.

Here's how to start playing.

Build genuine visibility first

Start sharing your entrepreneurial journey more honestly on platforms where your peers gather—like LinkedIn or tailored Slack communities:

• Share works-in-progress and ask specific questions

• Discuss real challenges you're facing (like Figma did)

• Celebrate others' wins more than your own

Don't treat this as content marketing. Think of it as building a public record of your thinking and challenges that makes you approachable and human.

PS: This was something I toed the line on—more than a few times—when running my first “real” business, so I created a simple Content Visibility Framework that outlines when to share vulnerably vs. when to keep challenges private. Use it to strike the right balance between openness and overexposure.

Engage meaningfully, not transactionally

When you see someone facing a challenge you've overcome:

• Offer help through specific, actionable comments

• If interest is shown in your advice, follow up privately with additional resources

• Ask questions that deepen their thinking rather than just providing answers

There’s a key difference between networking and connecting that you should heed, though: networking focuses on what you might get later. Connection focuses on what you can contribute now.

Create value persistently

Building meaningful professional relationships requires consistency:

• Set a weekly reminder to check in with one person you respect

• Share resources that made you think of them specifically

• Maintain relationships even when you don't need anything

As Figma demonstrated, the most valuable connections come from showing up consistently over time, not from rigid networking programs or transactional relationships.

I wish there were a more scalable approach, but there isn’t—and that’s the beauty of it. The long game of authentic connection always outperforms the short game of strategic networking.

Closing Thought

Entrepreneurship doesn't have to be a lonely road. Figma showed us that vulnerability isn't weakness. It's the foundation of genuine connection and, when paired with a strong work ethic, a powerful competitive advantage.

In a world obsessed with polished exteriors, there's remarkable power in simply being human. Your challenges and works-in-progress are precisely what make you relatable to others on the same journey.

Next week, I’m exploring the power of growing slowly and deliberately, to show you why patience is your greatest asset.

See you then.

Your Weekly Challenge

I'm challenging you to get a little uncomfortable by sharing some vulnerability this week. Post a genuine question or challenge you're facing on LinkedIn (or in a community you're part of).

Don't just post for validation—ask for specific feedback on something you're genuinely uncertain about. The goal isn't to look smart or polished, but to start building authentic connections.

Hit reply and let me know how it goes. What responses surprised you? Did anyone offer unexpected help?

I’ll start: apparently, people really like their feet held to the fire.

Told you—entrepreneurs are crazy. I love it.