Walking the Walk: What I've Learned From Founders (Now That I'm Becoming One… Again)
I have a confession to make.
Over the past ten months, I've been interviewing some of the most successful founders and CEOs on the planet for Social Currency— asking them how they built their companies, how they survived near “lose it all” experiences, how they made decisions that seemed crazy at the time. And I'd nod along, take notes, think wow, that's fascinating.
But I wasn't actually living any of it. I was a professional tourist in the world of entrepreneurship.
That's changed. I'm now building a new venture in media — and I can't say much more than that yet (we're mid-raise, and I'm trying not to jinx anything) — but I can tell you this: everything hits different when you're the one in the arena.
So today, I wanted to share something a little more personal today: the founder lessons that are actually landing now that I'm living them. I’m pulling some of my favorite conversations that I’ve had on the show to share how these lessons really hit home… and if you’re either an aspiring entrepreneur or currently shaping your own side hustle or full time venture, I hope these words bring as much value as they’re currently bringing to me.
1. "The first thing you have to do before you even pitch is have somebody’s attention."
— Jim McKelvey, Co-Founder of Square (link to interview here)
This one really resonates. Because here's the thing: I didn't start building this venture from zero. I started with you. With this newsletter. With the podcast. With years of showing up, building an audience, and earning trust.
And I didn't realize until recently how much of an advantage that actually is.
Most founders I talk to are trying to do two things at once: build the company and get people to care. They're cold-emailing potential investors, begging for press, trying to explain why anyone should pay attention to them. It's exhausting and inefficient.
By building a personal brand/online persona first, you get to skip ahead past the “This is who I am” step. This is what I’ve been able to do, and this is not because I'm special, but because I've been in the attention-earning business for years. When I walk into a room with a potential investor or partner, I’ve already felt that it’s a bit easier to share what I’m working on because I have a few proof points. They already have a sense of my taste, my values, my point of view.
Jim's point is deceptively simple: attention comes before the pitch. You can have the best deck in the world, but if no one's listening, it doesn't matter. The founders who win aren't just good at building — they're good at commanding the room before they enter it.
2. "I think the biggest mistake founders make is they think 'my idea is so secret I can't tell anybody, sign this NDA.' If you think your idea is what's protecting you, I promise you you're going to fail."
— Ankur Jain, Founder & CEO of Bilt (link to interview here)
There's a version of founder culture that treats ideas like precious cargo — locked away, and revealed only under NDA. I remember hearing Sara Blakely mention that this was her POV on building Spanx on a podcast. She famously didn’t tell a soul about Spanx initially because she didn’t want to invite competition. Obviously, Spanx ended up being a tremendous billion-dollar+ success. Ankur thinks that's backwards. And now that I'm building something myself, I side with Ankur on this one. And between you and I, I think Sara should have brought more people along on the ride before she launched her latest venture Sneex (but that’s a whole conversation that I’ll save for another newsletter).
Every week, I publish my takes on business and culture to hundreds of thousands of people. I talk about what I think is working, what's broken, what's next. I've interviewed the founders I admire most and asked them to reveal exactly how they built their companies. My entire brand is built on sharing ideas openly.
And here's what I've realized now that I'm building a new venture in media: that openness isn't a liability. It's the whole point (hence why seemingly every entrepreneur is now building in public).
Ankur told me that earning points on rent wasn't a revolutionary concept — getting it to work was the hard part. Stealth is overrated. Execution is everything.
3. "It's all about the people that you attract. And in my experience, the kind of people that I have gotten to work with, they need vision. Like they need to really believe in your vision, which means you need to believe in your vision. And if you don't believe in your vision, then why would anyone else take it seriously?"
— Cassandra Grey, Founder of Violet Grey (link to interview here)
Before you have a product, before you have revenue, all you have is the vision and conviction. And that conviction is either magnetic or it's not.
Cassandra had never built a company in the beauty space. She didn't go to business school. She barely graduated high school. But she had a vision for Violet Grey that was so clear, so fully realized in her mind, that she could walk into a room with Anna Wintour and hold her own. She attracted world-class collaborators not because she had the best résumé, but because she believed in what she was building so deeply that other people wanted to be part of it.
In the very early days of putting a business together and getting investors to believe in what you’re building, it’s essential that other people see that you know where you're going. Like you've already seen the future and you're just inviting them to help build it.
That kind of clarity doesn't come from a pitch deck. It comes from doing the internal work — the obsessive thinking about why this, why now, why me. Cassandra called it "courage of conviction." And as we all know, the best founders have so much conviction that it can sometimes border on delusion.
The Mindset Shift I Didn't Expect
As I’m going through the early days of building, I’m shifting how I see entrepreneurship: it’s less of a genre and I’ve started seeing it as a mirror. Every conversation I've had on this podcast has been preparing me for this, I just didn't know it yet. It’s really wild to look back on your career/decision trajectory and see how many of the pieces have a funny way of falling into place.
And now, during these podcast conversations, I'm not just taking notes. I'm applying them. More soon. For now, back to work.
— Sammi
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P.S. - If you see any typos in this newsletter, know that I did it on purpose a la The New Yorker via their style guide.
