(2026-10-12) Walling We Almost Sold Microconf For Seven Figures

Rob Walling (email): We almost sold MicroConf for seven figures.

When I came up as an entrepreneur, I learned direct response marketing.
I needed to make $2 for every dollar I put into the machine.
That mindset is a superpower. It forces you to build a business that generates revenue and profit from the start.

But it also trains you to think in the short term. For years, I rarely looked more than a few months out.
I never once asked where I wanted to be in ten years.
It took me a long time to learn that I needed to do both.

The Long Game Is a Fractal

From higher up, it's a decade or two of your career, where you start to notice a single thread tying everything you do together.

The long game at this altitude can also be brutal. One TinySeed company decided to move upmarket, from one- and two-person firms to teams of five to twenty. They estimated six to nine months. It took eighteen, and they nearly ran out of money more than once along the way. Playing the long game meant leaning in and believing there was something up ahead.

The Things You Can't See Coming

In 2011, Jason Cohen emailed to ask if I wanted to invest in his new company, WP Engine

it became the third most lucrative asset I've ever owned.

Here's the part I think about more often: why did Jason reach out to me at all? We'd never met. We'd never emailed. He'd been reading my blog, which I'd started in 2005, and he'd read my first book.

I'm not saying you need to start a podcast or build an audience. Plenty of people have built strong reputations without being audience builders. They got known because they were very good at what they did and talked about it just enough.

Did I know, when I started blogging in 2005, that it would lead to six books, 850 podcast episodes, MicroConf, and TinySeed? Absolutely not.

Then, in 2018, after I'd left my last startup, we received a seven-figure cash offer to buy MicroConf. We seriously considered it. I'd sold almost everything else already, and the idea of a fresh start in the tabletop gaming space sounded appealing. I think it would have been one of the deepest regrets of my life.

Instead, I took six months off and went on a founder retreat. And I realized something that should have been obvious years earlier: I'd been doing this work for free, on the side, for thirteen years. The blog, the books, the podcast, the conference. Nobody had to make me. I loved being an entrepreneur and being around other entrepreneurs, and there had been no community for people like us, so we built one. (warm niche)

I went all in. Everything people now think of as the MicroConf community came after that decision. So did a clear statement of my professional mission: to multiply the world's population of independent (indie), self-sustaining startups.

the moment I finally recognized the long game I'd already been playing.

How Do You Know You're Playing the Right One?

Honestly, it wasn't obvious to me until it was. Someone should have told me sooner.

The analogy I come back to is a plane flying from New York to Los Angeles. It doesn't fly a perfectly straight line. It makes course corrections the whole way as new information comes in. You're not going to know your long game at the start

What I did do, starting in my twenties, was stack skills. Hard work first, because my parents drilled it into me. Then web development. Then blogging. Then copywriting, because I realized I couldn't sell anything without it. Then marketing websites, SEO, pricing, AdWords, acquiring small products.

Of the three inputs to any outcome (hard work, luck, and skill), hard work is the one you control most. Luck is the one you control least. Skill sits in the middle, and it's the one that compounds. (compounding)

So here's the test I'd give you. Does your next step tie into your last step? Or are you bouncing from thing to thing, never building skills that relate to each other?
If they connect, you may already be playing a long game without realizing it.